4-amino-3-chlorobenzenethiol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Dimethylcyclohexylamine (22.86 g., 0.18 mole) in methylene chloride (125 ml.) is added dropwise to a stirred solution of 2-chloro-4-mercaptoaniline (27.0 g., 0.17 mole) and tert-butyl bromide (22.86 g., 0.18 mole) in methylene chloride (125 ml.) and the mixture is allowed to stir at room temperature for about 68 hours. An additional quantity of dimethylcyclohexylamine (2.3 g.) and tert-butyl bromide (2.5 g., 0.018 mole) is added and stirring is continued overnight. The reaction is poured into water, and the product is extracted with methylene chloride. The combined extracts are washed with dilute hydrochloric acid, water and dried. Removal of the drying agent and methylene chloride gives impure 2-chloro-4-tert-butylthioaniline as a beige solid. stirring is continued overnight the product is extracted with methylene chloride The combined extracts are washed with dilute hydrochloric acid, water dried Removal of the drying agent and methylene chloride

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-chloro-4-thiocyanoaniline (36.9 g., 0.20 mole) in ethanol (100-200 ml.) is added to a stirred solution of sodium sulfide nonahydrate (48.04 g., 0.20 mole) in water (100 ml.) and the mixture warmed (50° C.) for 90 minutes. The cool reaction mixture is poured into water (1 liter) and dilute hydrochloric acid added to bring the pH up to 6.0-6.5. The product is extracted with ether, the ether washed with water and then dried. Removal of the drying agent and ether leaves 2-chloro-4-mercaptoaniline as a yellow oil. The cool reaction mixture added The product is extracted with ether the ether washed with water dried Removal of the drying agent and ether