Reaction #586123

Reaction equation

water

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

cyclobutylmethyl bromide

potassium carbonate

→

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

Yield 21.6%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   OtherThe resulting reaction mixture
2. 2
   Extractionthe organic matters were extracted with 20 ml of ethyl acetate twice
3. 3
   Washwashed with 30 ml of water twice
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONthe ethyl acetate was distilled off under reduced pressure
6. 6
   OtherPurification of the residue by silica gel column chromatography

Procedure

0.9 g (3.3 mmol) of 2-mercapto-4-(3-trifluoromethylpyrazolyl)benzonitrile, 0.5 g (3.3 mmol) of cyclobutylmethyl bromide and 0.55 g (4.0 mmol) of potassium carbonate were stirred in 5 ml of N,N-dimethylformamide at room temperature overnight. The resulting reaction mixture was poured into 50 ml of water and the organic matters were extracted with 20 ml of ethyl acetate twice. The ethyl acetate layers were combined, then washed with 30 ml of water twice and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 0.24 g of 2-cyclobutylmethylthio-4-(3-trifluoromethylpyrazolyl)benzonitrile (yield 21.2%) as a pale yellow powder (m.p. 102-103° C.).

Source