Acetyl chloride → 1-Acetyl-4-methylimidazole

HRID 1980589Notes

Reaction equation

HRID 1980589 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[C:7](Cl)(=[O:9])[CH3:8]>C1(C)C=CC=CC=1>[C:7]([N:5]1[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]1)(=[O:9])[CH3:8]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 178418800HCID 178418800, compound

Product 1

HCID 109534921-Acetyl-4-methylimidazoleYield 50.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 50 g (609 mmol) of 4-methylimidazole in 250 ml of toluene was stirred at room temperature under nitrogen and 239 g (304 mmol) of acetyl chloride was added. The mixture was stirred at room temperature for 5 hours, filtered to remove insolubles and the filtrate concentrated giving 19 g (50%) of 1-acetyl-4-methyl-imidazole as a yellow oil which crystallizes on standing. nmr (CDCl3) (δ): 8.06 (s, 1H); 7.17 (s,1H); 2.57 (s, 3H); 2.23 (s, 3H).

Workup

  1. stirringThe mixture was stirred at room temperature for 5 hours
  2. filtrationfiltered
  3. customto remove insolubles
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-f1d03bceef45467e86be878176da4494
Source dataset
uspto-grants-1985_04
Patent number
US04510313

Reaction notes

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