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

HRID 1252353Notes

Reaction equation

HRID 1252353 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[S:7]([NH:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:9])=[O:8].BrC1SC=CC=1.[C-:21]#[N:22].[Na+]>CN(C)C=O>[C:21]([C:2]1[CH:6]=[CH:5][S:4][C:3]=1[S:7]([NH:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:9])=[O:8])#[N:22]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 138512-BromothiopheneHCID 140519253-bromo-N-tert-butylthiophene-2-sulfonamide

Product 1

HCID 142549393-Cyano-N-(1,1-dimethylethyl)thiophene-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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.

Workup

  1. extractionThe aqueous mixture was extracted with five, 200 mL portions of ethyl ether
  2. washthe combined extracts were washed with five, 150 mL portions of water
  3. washwash
  4. dry with materialAfter drying over magnesium sulfate, filtration and evaporation of the solvent 140.8 g of the desired product
  5. customwas obtained

Sources & evidence

ORD record
ord-a7a24be5e732421085ec0e9f866fe27b
Source dataset
uspto-grants-1988_05
Patent number
US04743290

Reaction notes

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