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[ CAS No. 40412-06-4 ] 2-(Thiophen-2-yl)ethyl 4-methylbenzenesulfonate Featured Image
  • [ CAS No. 40412-06-4 ] 2-(Thiophen-2-yl)ethyl 4-methylbenzenesulfonate
  • [ CAS No. 40412-06-4 ] 2-(Thiophen-2-yl)ethyl 4-methylbenzenesulfonate
  • [ CAS No. 40412-06-4 ] 2-(Thiophen-2-yl)ethyl 4-methylbenzenesulfonate
  • [ CAS No. 40412-06-4 ] 2-(Thiophen-2-yl)ethyl 4-methylbenzenesulfonate
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[ CAS No. 40412-06-4 ] 2-(Thiophen-2-yl)ethyl 4-methylbenzenesulfonate

Short Description:

Alternate Names:

2-Thiopheneethanol 2-(4-Methylbenzenesulfonate);

2-(2-Thienyl)ethyl Toluene-p-sulfonate;

2-(2-Thienyl)ethyl Tosylate;

2-(2-Thiophene)ethanol Tosylate;

2-(Thien-2-yl)ethyl 4-Methylbenzenesulfonate

Molecular Formula： C13H14O3S2

Molecular Weight: 282.38

Boilling Point:433.2°C at 760 mmHg

CAS: 40412-06-4

Product Detail

Product Tags

product standard

Appearance White to white like crystal
Purity 99% min.（GC）
2-thiophenethanol 0.5% max （GC）
paratoluensulfonyl chloride 0.5% max （GC）
Retest period 2 years

Product Details of [ 40412-06-4 ]

CAS No. :40412-06-4 MDL No. :MFCD05150366
Formula : C13H14O3S2 Boiling Point : 433.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :282.38 g/mol Pubchem ID :3682034
Synonyms :

Calculated chemistry of of [ 40412-06-4 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.23
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 72.76
TPSA : 79.99 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.84
Log Po/w (XLOGP3) : 3.24
Log Po/w (WLOGP) : 4.09
Log Po/w (MLOGP) : 2.65
Log Po/w (SILICOS-IT) : 3.68
Consensus Log Po/w : 3.3

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.75
Solubility : 0.0497 mg/ml ; 0.000176 mol/l
Class : Soluble
Log S (Ali) : -4.59
Solubility : 0.00721 mg/ml ; 0.0000255 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.04
Solubility : 0.00256 mg/ml ; 0.00000908 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.97

Safety of [ 40412-06-4 ]

Signal Word: Warning Class: N/A
Precautionary Statements: P261-P305+P351+P338 UN#: N/A
Hazard Statements: H302-H315-H319-H335 Packing Group: N/A
GHS Pictogram:

Application In Synthesis of [ 40412-06-4 ]

Upstream synthesis route of [ 40412-06-4 ]
Downstream synthetic route of [ 40412-06-4 ]
Upstream synthesis route of [ 40412-06-4 ]

vvv

Yield Reaction Conditions Operation in experiment
98% at 35℃; Cooling with ice (0.87 mol) of 2-thiopheneethanol and 184 g (0.97 mol) of p-toluenesulfonyl chloride were sequentially added to a 1 L three-necked flask, 98 g (0.97 mol) of triethylamine was dropwise added thereto under ice-water bath, And keep the temperature of the reaction liquid not higher than 20 DEG C, dropping finished, heating to 35 DEG C to continue stirring, respectively 24h, 27h sampling, TLC, until the reaction is complete, stop reaction, filtration, filter cake with appropriate amount of dichloromethane And the methylene chloride layer was dried with anhydrous sodium sulfate for 2 hours. The desiccant was filtered off and the desiccant was washed with a small amount of methylene chloride. The filtrate was decompressed in vacuo and the filtrate was evaporated under reduced pressure. Concentrated to constant weight to be brown oil, weighing 203g, yield 98percent,
96.37% With triethylamine In toluene at 5 - 30℃; for 20.8333 h; EXAMPLE 3
Preparation of 2-Thienylethyl Para-Toluenesulphonate (Formula VII) Using Toluene
400 liters of toluene and 163.2 kg of para-toluene sulfonyl chloride were charged into a clean and dry reactor followed by cooling to about 5° C. 100 kg of thiophene-2-ethanol was added at about 5° C. over about 20 minutes followed by addition of 130 kg of triethylamine over about 8 hours, 50 minutes.
The reaction mixture temperature was raised to about 30° C. followed by stirring for about 12 hours.
The reaction mass was filtered through a Nutsche filter and washed with 2*100 liters of toluene.
The reaction filtrate was transferred into another reactor followed by washing with 5*200 liters of water.
Organic and aqueous layers were separated and the organic layer was distilled completely at about below 70° C. under vacuum to afford 212 kg (yield: 96.37percent) of title compound.
Purity by GC: 95.59percent.
96.5% With triethylamine In dichloromethane at -5 - 20℃; for 2 h; 32.7 g (0.17 mol) of p-toluenesulfonyl chloride,40 ml of dichloromethane into the reaction flask, cooled to -5 ° C,20 g (0.16 mol)2-thiopheneethanol.28.4 g (0.28 mol) of triethylamine was slowly added dropwise and the temperature of the reaction solution was maintained at about 0 ° C.Plus Bi, incubated for 2h after the reaction was warmed to room temperature. 2-thiophene ethanol to be consumed until the raw materials, suction filtration,The solid was washed with a small amount of methylene chloride and the filtrate was washed with 50 ml of saturated sodium bicarbonate and dried over anhydrous sodium sulfate. Filtration, concentration of the filtrate, light brown solid precipitated out,Filtered, washed with a small amount of petroleum ether to white,That isP-toluenesulfonate-2-thiophene ethyl ester42.5 g, yield 96.5percent (HPLC purity 99percent)
95.5% With triethylamine In dichloromethane at 7.5 - 22.5℃; for 5 h; EXAMPLE 10
Preparation of 2-(2-Thiophene)Ethanol Tosylate (Formula VII) Using Dichloromethane
4 liters of dichloromethane was added into a reactor at a temperature of about 30° C., cooled to a temperature of about 7.5° C. to which was then added 1.784 kg of p-toluene sulphonyl chloride followed by 1 kg of thiophene-2-ethanol.
1.302 kg of triethylamine was added to the above reaction mass at a temperature of about 7.5° C. followed by slowly raising the temperature of the reaction mass to 22.5° C. for about 5 hours.
The obtained reaction mass was filtered through a pressure Nutsche filter, washed with methylene chloride (2*1 liter) and the mother liquor was collected and transferred into another reactor.
The organic layer was washed with water (5*2 liters).
The organic layer thus obtained was subjected to distillation at a temperature below 70° C. using hot water circulation.
The obtained residue was then cooled to about 30° C. to afford 2.1 kg (yield: 95.5percent) of title compound.
93.6% With triethylamine In toluene at 45℃; for 4 h; Example 1 0.2. Conversion of (S)-1 ,2,3,4-tetrahydro-5-hvdroxy-N-propyl- naphthalen-2-ammonium hydrobromide (VIII) into hydrochloride salt of rotigotine; 10.2.1. Preparation of 2-(2-Thienyl)ethyl-4-toluene sulfonate; 4-toluenesulfonyl chloride (162 g), toluene (363.3 g) and 2-(2-Thienyl)ethanol (104 g) are combined. Triethylamine (93 g) is added maintaining the temperature lower than 45° C. After 4hrs, the mixture is washed with aqueous phosphoric acid, aqueous sodium hydroxide and then water. The organic phase is distilled off under vacuum. Isopropanol (314 g) and heptanes (365.9 g) are added. The batch is crystallized by cooling and isolated at -15° C. The crystals are filtered and washed with heptanes (175 mL). The crystals are then dried under vacuum at room temperature until a melting point of > 30° C is obtained.Yield ( 214 g): 93.6 percentHPLC analyses confirmed purity >99percent and 100 percent assay in comparison to a reference standard.
93.6% With triethylamine In toluene at 45℃; for 4 h; 4-toluenesulfonyl chloride (162 g), toluene (363.3 g) and 2-(2-Thienyl)ethanol (104 g) are combined. Triethylamine (93 g) is added maintaining the temperature lower than 45° C. After 4 hrs, the mixture is washed with aqueous phosphoric acid, aqueous sodium hydroxide and then water. The organic phase is distilled off under vacuum. Isopropanol (314 g) and heptanes (365.9 g) are added. The batch is crystallized by cooling and isolated at −15° C. The crystals are filtered and washed with heptanes (175 mL). The crystals are then dried under vacuum at room temperature until a melting point of 30° C. is obtained. [0255] Yield (214 g): 93.6percent
90% With silica gel In dichloromethane for 2 h; Reflux The 12.8g (0.1mol) 2- (2- thienyl) ethanol, 1000mL of dichloromethane, 21.0g (0.12mol) of p-toluenesulfonic acid chloride and 10.0g of silica gel into the reaction flask, the reaction was refluxed for 2h, cooled, filtered to remove silica gel.The reaction mixture was washed successively with distilled water, saturated sodium carbonate solution, brine, then the methylene chloride solvent was removed by distillation under reduced pressure, to give 26.0g of p-toluenesulfonic acid Preparation of 2- (2-thienyl) ethyl ester, 90percent yield .
Downstream synthetic route of [ 40412-06-4 ]

vvv

Yield Reaction Conditions Operation in experiment
98% With triethylamine; at 35℃;Cooling with ice; (0.87 mol) of 2-thiopheneethanol and 184 g (0.97 mol) of p-toluenesulfonyl chloride were sequentially added to a 1 L three-necked flask, 98 g (0.97 mol) of triethylamine was dropwise added thereto under ice-water bath, And keep the temperature of the reaction liquid not higher than 20 DEG C, dropping finished, heating to 35 DEG C to continue stirring, respectively 24h, 27h sampling, TLC, until the reaction is complete, stop reaction, filtration, filter cake with appropriate amount of dichloromethane And the methylene chloride layer was dried with anhydrous sodium sulfate for 2 hours. The desiccant was filtered off and the desiccant was washed with a small amount of methylene chloride. The filtrate was decompressed in vacuo and the filtrate was evaporated under reduced pressure. Concentrated to constant weight to be brown oil, weighing 203g, yield 98%,
96.37% With triethylamine; In toluene; at 5 - 30℃; for 20.8333h;Product distribution / selectivity; EXAMPLE 3 Preparation of 2-Thienylethyl Para-Toluenesulphonate (Formula VII) Using Toluene 400 liters of toluene and 163.2 kg of para-toluene sulfonyl chloride were charged into a clean and dry reactor followed by cooling to about 5 C. 100 kg of thiophene-2-ethanol was added at about 5 C. over about 20 minutes followed by addition of 130 kg of triethylamine over about 8 hours, 50 minutes. The reaction mixture temperature was raised to about 30 C. followed by stirring for about 12 hours. The reaction mass was filtered through a Nutsche filter and washed with 2*100 liters of toluene. The reaction filtrate was transferred into another reactor followed by washing with 5*200 liters of water. Organic and aqueous layers were separated and the organic layer was distilled completely at about below 70 C. under vacuum to afford 212 kg (yield: 96.37%) of title compound. Purity by GC: 95.59%.
96.5% With triethylamine; In dichloromethane; at -5 - 20℃; for 2h; 32.7 g (0.17 mol) of p-toluenesulfonyl chloride,40 ml of dichloromethane into the reaction flask, cooled to -5 C,20 g (0.16 mol)2-thiopheneethanol.28.4 g (0.28 mol) of triethylamine was slowly added dropwise and the temperature of the reaction solution was maintained at about 0 C.Plus Bi, incubated for 2h after the reaction was warmed to room temperature. 2-thiophene ethanol to be consumed until the raw materials, suction filtration,The solid was washed with a small amount of methylene chloride and the filtrate was washed with 50 ml of saturated sodium bicarbonate and dried over anhydrous sodium sulfate. Filtration, concentration of the filtrate, light brown solid precipitated out,Filtered, washed with a small amount of petroleum ether to white,That isP-toluenesulfonate-2-thiophene ethyl ester42.5 g, yield 96.5% (HPLC purity 99%)
95.5% With triethylamine; In dichloromethane; at 7.5 - 22.5℃; for 5h;Product distribution / selectivity; EXAMPLE 10 Preparation of 2-(2-Thiophene)Ethanol Tosylate (Formula VII) Using Dichloromethane 4 liters of dichloromethane was added into a reactor at a temperature of about 30 C., cooled to a temperature of about 7.5 C. to which was then added 1.784 kg of p-toluene sulphonyl chloride followed by 1 kg of thiophene-2-ethanol. 1.302 kg of triethylamine was added to the above reaction mass at a temperature of about 7.5 C. followed by slowly raising the temperature of the reaction mass to 22.5 C. for about 5 hours. The obtained reaction mass was filtered through a pressure Nutsche filter, washed with methylene chloride (2*1 liter) and the mother liquor was collected and transferred into another reactor. The organic layer was washed with water (5*2 liters). The organic layer thus obtained was subjected to distillation at a temperature below 70 C. using hot water circulation. The obtained residue was then cooled to about 30 C. to afford 2.1 kg (yield: 95.5%) of title compound.
93.6% With triethylamine; In toluene; at 45℃; for 4h; Example 1 0.2. Conversion of (S)-1 ,2,3,4-tetrahydro-5-hvdroxy-N-propyl- naphthalen-2-ammonium hydrobromide (VIII) into hydrochloride salt of rotigotine; 10.2.1. Preparation of 2-(2-Thienyl)ethyl-4-toluene sulfonate; 4-toluenesulfonyl chloride (162 g), toluene (363.3 g) and 2-(2-Thienyl)ethanol (104 g) are combined. Triethylamine (93 g) is added maintaining the temperature lower than 45 C. After 4hrs, the mixture is washed with aqueous phosphoric acid, aqueous sodium hydroxide and then water. The organic phase is distilled off under vacuum. Isopropanol (314 g) and heptanes (365.9 g) are added. The batch is crystallized by cooling and isolated at -15 C. The crystals are filtered and washed with heptanes (175 mL). The crystals are then dried under vacuum at room temperature until a melting point of > 30 C is obtained.Yield ( 214 g): 93.6 %HPLC analyses confirmed purity >99% and 100 % assay in comparison to a reference standard.
93.6% With triethylamine; In toluene; at 45℃; for 4h; 4-toluenesulfonyl chloride (162 g), toluene (363.3 g) and 2-(2-Thienyl)ethanol (104 g) are combined. Triethylamine (93 g) is added maintaining the temperature lower than 45 C. After 4 hrs, the mixture is washed with aqueous phosphoric acid, aqueous sodium hydroxide and then water. The organic phase is distilled off under vacuum. Isopropanol (314 g) and heptanes (365.9 g) are added. The batch is crystallized by cooling and isolated at -15 C. The crystals are filtered and washed with heptanes (175 mL). The crystals are then dried under vacuum at room temperature until a melting point of 30 C. is obtained. [0255] Yield (214 g): 93.6%
90% With silica gel; In dichloromethane; for 2h;Reflux; The 12.8g (0.1mol) 2- (2- thienyl) ethanol, 1000mL of dichloromethane, 21.0g (0.12mol) of p-toluenesulfonic acid chloride and 10.0g of silica gel into the reaction flask, the reaction was refluxed for 2h, cooled, filtered to remove silica gel.The reaction mixture was washed successively with distilled water, saturated sodium carbonate solution, brine, then the methylene chloride solvent was removed by distillation under reduced pressure, to give 26.0g of p-toluenesulfonic acid Preparation of 2- (2-thienyl) ethyl ester, 90% yield .
In pyridine; water; (a) 2-(2-Hydroxyethyl)thiophene tosylate Toluene-4-sulphonyl chloride (4.125 g) was added portionwise over 5 mins to an ice-cold solution of 2-(2-hydroxyethyl)thiophene (1.723 g) in anhydrous pyridine (20 ml) and the resulting pale yellow solution was stirred at 0 C. After 3 h the reaction mixture was poured into vigorously stirred water (160 ml) producing a precipitate. After cooling the solid was collected and washed with water to give white crystals of the title tosylate (3.555 g), m.p. 33-34 C., lambdamax (EtOH) 227 nm (E11 612).
With triethylamine; In butanone; at 0 - 30℃; Example 1 Preparation of 2-(2-Thienyl)-ethyl para-toluenesulfonate A mixture of p-toluenesulfonyl chloride (328 gm) and 2-(2-thienyl)-ethanol (200 gm) in methyl ethyl ketone (1000 ml) was cooled to 0C. This was followed by drop wise addition of triethyl amine (283.1 ml) at 0-5C over a period of 1 to 2 hours, and the reaction mass was stirred for 12 to 15 hours at 25-3O0C. The resulting mass was filtered and washed with methyl ethyl ketone (500 ml). The resulting organic layer was washed with water (500 ml) followed by washings with saturated sodium bicarbonate solution (500 ml) and brine solution (500 ml). The resulting organic layer was distilled under vacuum at below 50C to give 2-(2- thienyl)-ethyl para-toluenesulfonate as an oily mass (Weight of the oil: 505 gm; Purity by HPLC: 97%).
With triethylamine; In butanone; at 0 - 30℃; Example 1 Preparation of 2-(2-Thienyl)-ethyl para-toluenesulfonate A mixture of p-toluenesulfonyl chloride (328 gm) and 2-(2-thienyl)-ethanol (200 gm) in methyl ethyl ketone (1000 ml) was cooled to 0 C. This was followed by drop wise addition of triethyl amine (283.1 ml) at 0-5 C. over a period of 1 to 2 hours, and the reaction mass was stirred for 12 to 15 hours at 25-30 C. The resulting mass was filtered and washed with methyl ethyl ketone (500 ml). The resulting organic layer was washed with water (500 ml) followed by washings with saturated sodium bicarbonate solution (500 ml) and brine solution (500 ml). The resulting organic layer was distilled under vacuum at below 50 C. to give 2-(2-thienyl)-ethyl para-toluenesulfonate as an oily mass (Weight of the oil: 505 gm; Purity by HPLC: 97%).
With potassium carbonate; In toluene; at 0 - 20℃; for 3.5h; 500 ml of toluene was added to a 1000 ml reaction flask,50gThiophene ethanolAnd 80 g of p-toluenesulfonyl chloride,Turn on agitation,Controlled temperature was added dropwise at 0 C64 g of potassium carbonate,The addition was continued for about 30 min, Dropping finished warming to 20 C reaction for 3 hours,To the reaction solution was added 400 ml of water,Washed twice,The washed toluene layer was directly used for the next reaction.
With N-ethyl-N,N-diisopropylamine; In toluene; at 0 - 20℃; for 3.5h; 500 ml of toluene was added to a 1000 ml reaction flask, 50 g of thiophene ethanol and 92 g of p-toluenesulfonyl chloride, stirred at 0 C, 62 g of N, N-diisopropylethylamine was dropped for about 30min. When dropping was completed, mixture was heated to 20 C and reacted for 3 hours. To the reaction solution was added 400 ml of water, washed twice, the washed toluene layer was directly used for the next reaction.
With triethylamine; In toluene; at 0 - 20℃; for 3h; 500 ml of toluene, 50 g of thiophene ethanol and 80 g of p-toluenesulfonyl chloride were placed in a 1000 ml reaction flask,And the temperature was raised to 20 C for 3 hours. 400 ml of water was added to the reaction solution, washed twice, washed with toluene, Layer directly to the next step reaction.
With potassium carbonate; In toluene; at 0 - 20℃; for 3.5h; 500 ml of toluene, 50 g of thiophene ethanol and 107 g of p-toluenesulfonyl chloride were placed in a 1000 ml reaction flask, agitation was turned on, the temperature was controlled at 0 C, dropwise addition of 64g potassium carbonate, addition lasted about 30min, after which it was warmed to 20 C and reacted for 3 hours, to the reaction solution was added 400 ml of water, washed twice, and the washed toluene layer was directly used for the next reaction.
With triethylamine; In toluene; at 0 - 25℃; for 3.5h; Example 1The preparation method of ticlopidine hydrochloride as shown in Fig. 2 comprises the following steps:1. p-toluenesulfonyl protection:In a 1000 ml reaction flask, 500 ml of toluene, 50 g of thiophene ethanol and 80 g of p-toluenesulfonyl chloride were charged and stirred to controlAt a temperature of 0 C, 47 g of triethylamine was added dropwise, dropping for about 30 min, and the temperature was raised to 25 C for 3 hours.Add 400ml of water, washed twice, washed with toluene layer directly to the next step reaction.2. Condensation reactionThe reaction solution of toluene in the previous step was added to a 1000 ml reaction flask, followed by the addition of 114 g of o-chlorobenzylamine and heating to 90 C for 3 hours. After the reaction, the mixture was cooled to 25 C and stirred for 1 hour. The filtrate was added with 200 ml of water, and hydrochloric acidAdjust the pH of the system to 8.5, stratify the upper layer of toluene and continue dropping hydrochloric acid to adjust the pH to 5, then cool the system to 2 CThe crystals were mixed for 4 hours and filtered, and the filter cake was dried in vacuo at 50 C to give 96 g of the condensate hydrochloride.3 ? Closed loop reactionTo the 1000 ml reaction flask was added 96 g of the condensate hydrochloride, 400 ml of 1,3-dioxane and 5 ml of hydrochloric acid,To 90 C for 6 hours. After the reaction, the mixture was cooled to 7 C and stirred for 3 hours. The filter cake was washed with a small amount of 1,3-dioxetaneAfter 50 C vacuum drying, 95 g of ticlopidine hydrochloride was obtained4 ? RefinedIn a 1000 ml reaction flask, 95 g of crude ticlopidine hydrochloride and 500 ml of absolute ethanol were added and heated to 72 C with stirring,About 10 minutes after the solid is completely dissolved by adding 2g activated carbon, insulation bleaching 20 minutes after the hot filter, the filtrate gradually coolingThe crystals were crystallized at 4 C for 4 hours and filtered. The filter cake was washed with a small amount of absolute ethanol and dried in vacuo at 50 C to give 91 g of tithiol hydrochloridePrecision products. Total yield 82%, purity 99.9%
With sodium hydroxide; In water; toluene; at 10 - 55℃; for 11h; In a three-necked flask, 97 g of p-toluenesulfonyl chloride and 180 ml of toluene were placed.Stir and dissolve, filter, keep warm at 15-20 C,60 g of 2-thiopheneethanol and 60 ml of toluene were placed in a three-necked flask.120g 40% aqueous sodium hydroxide, stirring,A solution of 97 g of p-toluenesulfonyl chloride dissolved in 180 ml of toluene was added dropwise at 10-20 C, and the mixture was stirred for 3 h, then heated to 45-55 C for 8 h, and allowed to stand for stratification.The organic phase is depressurized to remove toluene to give 2-(2-thiophene)ethanol p-toluenesulfonate.Reddish brown oil; the molecular formula is as follows:
235.1 g With sodium hydroxide; In chloroform; at 0 - 5℃; for 12h; To the reaction flask, the above step 2-thiophene ethanol: 112 g, chloroform 600 g, PTSC 249.4 g, and the mixture was cooled to 0-5 C.Add 834g of 10% by mass sodium hydroxide solution, control the temperature 0-5 C, keep warm for 12h, add hydrochloric acid to pH=12, layer, the water layer is extracted with 300g chloroform, and the chloroform layer is combined. After washing with 100 g of water, the organic layer was distilled to dryness to give 2-thiopheneethanol p-toluenesulfonate: 235.1 g yield 95.3%, purity 99.5%.

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