Reaction #1339535

Reaction equation

sodium cyanide

3-bromo-N-(1,1-dimethylethyl)thiophene-2-sulfonamide

bromothiophene

→

3-Cyano-N-(1,1-dimethylethyl)thiophene-2-sulfonamide

Solvents

dimethylformamide

Conditions

Workup

1. 1
   ExtractionThe aqueous mixture was extracted with five, 200 mL portions of ethyl ether
2. 2
   Washthe combined extracts were washed with five, 150 mL portions of water
3. 3
   Washwash
4. 4
   DryingAfter drying over magnesium sulfate, filtration and evaporation of the solvent 140.8 g of the desired product
5. 5
   Otherwas obtained

Procedure

A mixture of 197.7 g of 3-bromo-N-(1,1-dimethylethyl)thiophene-2-sulfonamide, 195.9 g of cuprous cyanide and 500 mL of dimethylformamide was heated to 150° for two one half hours at which time none of the bromothiophene remained as indicated by thin layer chromatography. The reaction was cooled to room temperature and poured into 1500 mL of 10% aqueous sodium cyanide. The aqueous mixture was extracted with five, 200 mL portions of ethyl ether and the combined extracts were washed with five, 150 mL portions of water followed by one, 200 mL aqueous sodium chloride wash. After drying over magnesium sulfate, filtration and evaporation of the solvent 140.8 g of the desired product was obtained.

Source