Potassium Cyanide → HCID 22130162, compound

HRID 1857727Notes

Reaction equation

HRID 1857727 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH3:18])[N:6]([CH3:17])[C:7]=1[S:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[CH:10]=1.[C-:19]#[N:20].[K+]>CN(C)C=O>[CH3:17][N:6]1[C:7]([S:8][C:9]2[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[CH:10]=2)=[C:3]([CH2:2][C:19]#[N:20])[N:4]=[C:5]1[CH3:18]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 22130786HCID 22130786, compound

Product 1

HCID 22130162HCID 22130162, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

In 5.6 ml of dry dimethylformamide was dissolved 280 mg (1.0 mmol) of 4-chloromethyl-1,2-dimethyl-5-(3,5-dimethylphenylthio)-1H-imidazole (42c). Added was 98 mg (1.5 mmol) of potassium cyanide, and the mixture was heated at 50° C. for 5 hours. To the reaction mixture, ice-water was added, extracted with diethyl ether, the extract was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate) to obtain 114 mg of [1,2-dimethyl-5-(3,5-dimethylphenylthio)-1H-imidazol-4-yl]acetonitrile (42d) (yield 42%).

Workup

  1. additionAdded
  2. extractionextracted with diethyl ether
  3. washthe extract was washed with water
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-1037ed0169ef4149b0c7bc08d4a7be7f
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

Loading…