Potassium Cyanide → HCID 22130162, compound

HRID 1416028Notes

Reaction equation

HRID 1416028 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%). mp 81-82° C.

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)to

Sources & evidence

ORD record
ord-9f3e7cf5b96740f59463a6ef6fce718f
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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