Dimethylformamide → 4-[4-(2-Methyl-1-imidazolyl)phenyl]-3-methyl-4-oxobutyronitrile

HRID 1583288Notes

Reaction equation

HRID 1583288 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.CN(C)C=O.[C-]#N.[Na+].[C:23](#[N:27])[CH:24]=[CH:25][CH3:26]>O>[CH3:1][C:2]1[N:3]([C:7]2[CH:14]=[CH:13][C:10]([C:11](=[O:12])[CH:25]([CH3:26])[CH2:24][C:23]#[N:27])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 209132-ButenenitrileHCID 31596624-(2-Methyl-1H-imidazol-1-yl)benzaldehyde

Product 1

HCID 132338764-[4-(2-Methyl-1-imidazolyl)phenyl]-3-methyl-4-oxobutyronitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

To a mixture of 33.6 g of 4-(2-methyl-1-imidazolyl)benzaldehyde and 400 ml of dimethylformamide under a nitrogen atmosphere was added 0.78 g of sodium cyanide and then with stirring at 30° C. 10.7 g of 2-butenenitrile was added dropwise. The reaction mixture was stirred at 25° C. under nitrogen for another 16 hours. Following the addition of one liter of water the mixture was extracted with chloroform, and the chloroform phase was washed with water, dried over sodium sulfate, and concentrated. The residue was purified by column chromatography (silica gel/chloroform) and then reprecipitated with chloroform/hexane.

Workup

  1. stirringThe reaction mixture was stirred at 25° C. under nitrogen for another 16 hours
  2. extractionwas extracted with chloroform
  3. washthe chloroform phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica gel/chloroform)
  7. customreprecipitated with chloroform/hexane

Sources & evidence

ORD record
ord-6f6eb74cac7b4f0ab04eeacc4420f873
Source dataset
uspto-grants-1985_11
Patent number
US04551455

Reaction notes

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