Reaction #586147

Reaction equation

water

2-chloro-4-(3-trifluoromethylpyrazolyl)benzonitrile

sodium sulfide

→

2-mercapto-4-(3-trifluoromethylpyrazolyl)benzonitrile

Yield 97.6%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   Washwashed with 30 ml of ethyl acetate
2. 2
   Extractionextracted with 50 ml of ethyl acetate twice
3. 3
   Washwashed with 50 ml of water twice
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONThe ethyl acetate was distilled off under reduced pressure

Procedure

5.0 g (18.4 mmol) of 2-chloro-4-(3-trifluoromethylpyrazolyl)benzonitrile in N,N-dimethylformamide was stirred together with 1.86 g (23.9 mmol) of sodium sulfide at 120° C. for 30 minutes. The reaction mixture was cooled to room temperature, mixed with 100 ml of water, washed with 30 ml of ethyl acetate, and the aqueous layer was adjusted at pH 5-6 with citric acid, and extracted with 50 ml of ethyl acetate twice. The ethyl acetate layers were combined, washed with 50 ml of water twice and dried over anhydrous magnesium sulfate. The ethyl acetate was distilled off under reduced pressure to obtain 2-mercapto-4-(3-trifluoromethylpyrazolyl)benzonitrile (yield 97.6%) as a pale yellow powder, which was used in Example 1 (2) as the starting material.

Source