2-cyclohexylsulfanylaniline

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

Procedure: In 10 ml of pyridine was dissolved 2.0 g of 2-(cyclohexylthio)aniline obtained in Example 2 (2), 1.2 g of ethanesulfonyl chloride was added dropwise under ice cooling, and then the mixture was stirred at room temperature overnight. The reaction solution was poured into ice water, made acidic with dilute hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed, in turn, with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (eluent:n-hexaneethyl acetate=10:1) to give 2.7 g of N-[2-(cyclohexylthio)phenyl]ethanesulfonamide as an oil. was added dropwise under ice cooling extracted with ethyl acetate The ethyl acetate layer was washed, in turn, with water a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate The solvent was evaporated the resulting residue was purified by silica gel column chromatography (eluent:n-hexaneethyl acetate=10:1)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 8.5 g of 2-(cyclohexylthio)nitrobenzene, 9.6 g of iron powder, 0.61 g of ammonium chloride and 22 ml of water was stirred on heating at 90° C. for 3 hours. The temperature of the reaction solution was returned to room temperature, the reaction solution was filtered by Selite and extracted with dichloromethane. The dichloromethane layer was washed, in turn, with water and a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated to give 7.3 g of 2-(cyclohexylthio)aniline as a yellow oil. was returned to room temperature the reaction solution was filtered by Selite extracted with dichloromethane The dichloromethane layer was washed, in turn, with water a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate The solvent was evaporated

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 8.5 g of 2-(cyclohexylthio)nitrobenzene, 9.6 g of iron powder, 0.61 g of ammonium chloride and 22 ml of water was stirred on heating at 90° C. for 3 hours. The temperature of the reaction solution was returned to room temperature, the reaction solution was filtered by Selite and extracted with dichloromethane. The dichloromethane layer was washed, in turn, with water and a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated to give 7.3 g of 2-(cyclohexylthio)aniline as a yellow oil. was returned to room temperature the reaction solution was filtered by Selite extracted with dichloromethane The dichloromethane layer was washed, in turn, with water a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate The solvent was evaporated

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

Procedure: In 10 ml of pyridine was dissolved 2.0 g of 2-(cyclohexylthio)aniline obtained in Example 2 (2), 1.2 g of ethanesulfonyl chloride was added dropwise under ice cooling, and then the mixture was stirred at room temperature overnight. The reaction solution was poured into ice water, made acidic with dilute hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed, in turn, with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (eluent:n-hexaneethyl acetate=10:1) to give 2.7 g of N-[2-(cyclohexylthio)phenyl]ethanesulfonamide as an oil. was added dropwise under ice cooling extracted with ethyl acetate The ethyl acetate layer was washed, in turn, with water a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate The solvent was evaporated the resulting residue was purified by silica gel column chromatography (eluent:n-hexaneethyl acetate=10:1)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 8.5 g of 2-(cyclohexylthio)nitrobenzene, 9.6 g of iron powder, 0.61 g of ammonium chloride and 22 ml of water was stirred on heating at 90° C. for 3 hours. The temperature of the reaction solution was returned to room temperature, the reaction solution was filtered by Selite and extracted with dichloromethane. The dichloromethane layer was washed, in turn, with water and a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated to give 7.3 g of 2-(cyclohexylthio)aniline as a yellow oil. was returned to room temperature the reaction solution was filtered by Selite extracted with dichloromethane The dichloromethane layer was washed, in turn, with water a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate The solvent was evaporated