1-phenylethanethiol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suitable reactor equipped with temperature controlling means and stirring means, there are charged, while maintaining the temperature at about room temperature, N-chlorosuccinimide (about 0.30 mole) in 400 ml of benzene and 1-phenylethanethiol (about 0.30 mole) in 50 ml of benzene. After stirring the reaction mixture 10 minutes, triethylamine (0.32 mole) in 50 ml of benzene is added dropwise. The benzene mixture is stirred one hour and then filtered. The filtrate is washed three times with 250 ml portions of water and then subjected to vacuum with heating to strip off volatile components. A crystalline residue is recrystallized from ethanol to give 26 grams of N-(α-methylbenzylthio)succinimide, m.p. 121°-125° C. To a suitable reactor equipped with temperature are charged while maintaining the temperature at about room temperature is added dropwise filtered The filtrate is washed three times with 250 ml portions of water with heating A crystalline residue is recrystallized from ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 500 ml. three-necked flask were charged 108 g. (0.78 mole) 1-phenyl-ethanethiol, 126 g. (0.78 mole) vinyltrichlorosilane and 1.2 g. (0.5 weight percent) azobisisobutyronitrile catalyst. The contents were heated and stirred for 6 hours at 80°-90°C. Fractional distillation of the reaction mixture gave the product fraction, Cl3SiCH2CH2SCH(CH3)C6H5, b.p. 110°/0.53 mm Hg. Vapor phase chromatographic analysis of the distilled product (120 g.) showed it contained a mixture of alpha and beta isomers. Yield of (1-phenylethylthio)ethyltrichlorosilane was 85 percent, based on ViSiCl3 reacted. three-necked flask were charged 108 g The contents were heated Fractional distillation of the reaction mixture

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At room temperature, 13.8 g of 1-mercapto-1-phenylethane is dissolved in 50 mL of butyryl chloride. The mixture is stirred at room temperature for 6 hours. It is then cooled down to 0° C. and the reaction is quenched by careful addition of 100 ml of dry methanol in small portions. The mixture is then washed with bicarbonate, dried over magnesium sulfate, filtered and concentrated to give the butyrated compound in 98% yield. It is then cooled down to 0° C. the reaction is quenched by careful addition of 100 ml of dry methanol in small portions The mixture is then washed with bicarbonate dried over magnesium sulfate filtered concentrated to give the butyrated compound in 98% yield

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At room temperature, 13.8 g of 1-mercapto-1-phenylethane is dissolved in 50 mL of butyryl chloride. The mixture is stirred at room temperature for 6 hours. It is then cooled down to 0° C. and the reaction is quenched by careful addition of 100 ml of dry methanol in small portions. The mixture is then washed with bicarbonate, dried over magnesium sulfate, filtered and concentrated to give the butyrated compound in 98% yield. It is then cooled down to 0° C. the reaction is quenched by careful addition of 100 ml of dry methanol in small portions The mixture is then washed with bicarbonate dried over magnesium sulfate filtered concentrated to give the butyrated compound in 98% yield

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a synthesis carried out according to Hoppe, et al., Angew. Chem. Int. Ed., 36(24), 2784 (1997), at room temperature, 2.1 g of lithium aluminum hydride and 100 mL of methyl tertiary butyl ether are added to a 250 mL round-bottom flask. To this suspension 18 g of thioacetic acid S-(1-phenyl-ethyl)ester in 50 mL MTBE is added. The mixture is stirred for 15 h at room temperature. 5 mL of ethyl acetate and 2.5 mL of sodium hydroxide (1 M in water) are added. The reaction mixture is filtered over a sodium sulphate plug. The filtrate is concentrated to give 13.7 g of a yellow liquid which is purified by distillation. The reaction mixture is filtered over a sodium sulphate plug The filtrate is concentrated

Conditions: temp:18.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5.6 g (50 mmol) of potassium t-butoxide in 100 ml of tetrahydrofuran is added 8.7 ml (8.94 g, 60 mmol) of 92% 1-phenylethylmercaptan while maintaining the temperature of the reaction mixture between 20° and 25° C. The resulting suspension is cooled to 18° C. and 4.35 ml (72 mmol) of carbon disulfide is added thereto. The yellow solution which forms is stirred for 0.5 hours and then 3.23 ml (50 mmol) of chloroacetonitrile is added while the temperature of the reaction mixture is maintained at about 20° C. After stirring for 0.5 hour, the mixture is concentrated in vacuo. The residue is taken up in ether and the ether solution washed with water, brine, dried with Na2SO4 and concentrated in vacuo. The residue is chromatographed on a silica gel dry-column and eluted with 1:2 CH2Cl2 -hexane. The yellow band is collected to give 11.25 g (89%) of a yellow oil, cyanomethyl α-methylbenzyl trithiocarbonate. while maintaining the temperature of the reaction mixture between 20° and 25° C is maintained at about 20° C After stirring for 0.5 hour the mixture is concentrated in vacuo the ether solution washed with water, brine dried with Na2SO4 concentrated in vacuo The residue is chromatographed on a silica gel dry-column eluted with 1:2 CH2Cl2 -hexane The yellow band is collected

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suitable reactor equipped with temperature controlling means and stirring means, there are charged, while maintaining the temperature at about room temperature, N-chlorosuccinimide (about 0.30 mole) in 400 ml of benzene and 1-phenylethanethiol (about 0.30 mole) in 50 ml of benzene. After stirring the reaction mixture 10 minutes, triethylamine (0.32 mole) in 50 ml of benzene is added dropwise. The benzene mixture is stirred one hour and then filtered. The filtrate is washed three times with 250 ml portions of water and then subjected to vacuum with heating to strip off volatile components. A crystalline residue is recrystallized from ethanol to give 26 grams of N-(α-methylbenzylthio)succinimide, m.p. 121-125°C. To a suitable reactor equipped with temperature are charged while maintaining the temperature at about room temperature is added dropwise filtered The filtrate is washed three times with 250 ml portions of water with heating A crystalline residue is recrystallized from ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suitable reactor equipped with temperature controlling means and stirring means, there are charged, while maintaining the temperature at about room temperature, N-chlorosuccinimide (about 0.30 mole) in 400 ml of benzene and 1-phenylethanethiol (about 0.30 mole) in 50 ml of benzene. After stirring the reaction mixture 10 minutes, triethylamine (0.32 mole) in 50 ml of benzene is added dropwise. The benzene mixture is stirred one hour and then filtered. The filtrate is washed three times with 250 ml portions of water and then subjected to vacuum with heating to strip off volatile components. A crystalline residue is recrystallized from ethanol to give 26 grams of N-(α-methylbenzylthio)succinimide, m.p. 121°-125° C. To a suitable reactor equipped with temperature are charged while maintaining the temperature at about room temperature is added dropwise filtered The filtrate is washed three times with 250 ml portions of water with heating A crystalline residue is recrystallized from ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 500 ml. three-necked flask were charged 108 g. (0.78 mole) 1-phenyl-ethanethiol, 126 g. (0.78 mole) vinyltrichlorosilane and 1.2 g. (0.5 weight percent) azobisisobutyronitrile catalyst. The contents were heated and stirred for 6 hours at 80°-90°C. Fractional distillation of the reaction mixture gave the product fraction, Cl3SiCH2CH2SCH(CH3)C6H5, b.p. 110°/0.53 mm Hg. Vapor phase chromatographic analysis of the distilled product (120 g.) showed it contained a mixture of alpha and beta isomers. Yield of (1-phenylethylthio)ethyltrichlorosilane was 85 percent, based on ViSiCl3 reacted. three-necked flask were charged 108 g The contents were heated Fractional distillation of the reaction mixture

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At room temperature, 13.8 g of 1-mercapto-1-phenylethane is dissolved in 50 mL of butyryl chloride. The mixture is stirred at room temperature for 6 hours. It is then cooled down to 0° C. and the reaction is quenched by careful addition of 100 ml of dry methanol in small portions. The mixture is then washed with bicarbonate, dried over magnesium sulfate, filtered and concentrated to give the butyrated compound in 98% yield. It is then cooled down to 0° C. the reaction is quenched by careful addition of 100 ml of dry methanol in small portions The mixture is then washed with bicarbonate dried over magnesium sulfate filtered concentrated to give the butyrated compound in 98% yield

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a synthesis carried out according to Hoppe, et al., Angew. Chem. Int. Ed., 36(24), 2784 (1997), at room temperature, 2.1 g of lithium aluminum hydride and 100 mL of methyl tertiary butyl ether are added to a 250 mL round-bottom flask. To this suspension 18 g of thioacetic acid S-(1-phenyl-ethyl)ester in 50 mL MTBE is added. The mixture is stirred for 15 h at room temperature. 5 mL of ethyl acetate and 2.5 mL of sodium hydroxide (1 M in water) are added. The reaction mixture is filtered over a sodium sulphate plug. The filtrate is concentrated to give 13.7 g of a yellow liquid which is purified by distillation. The reaction mixture is filtered over a sodium sulphate plug The filtrate is concentrated