1-Methylimidazole → 2,2,2-Trichloro-1-(1-methylimidazol-2-yl)ethanone

HRID 1025550Notes

Reaction equation

HRID 1025550 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[Cl:7][C:8]([Cl:13])([Cl:12])[C:9](Cl)=[O:10].C(N(CC)CC)C>C(Cl)Cl>[Cl:7][C:8]([Cl:13])([Cl:12])[C:9]([C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=1)=[O:10]

Participants

5

Reactant 3

HCID 13901-MethylimidazoleHCID 6420Trichloroacetyl chlorideHCID 8471Triethylamine

Product 1

HCID 112991222,2,2-Trichloro-1-(1-methylimidazol-2-yl)ethanoneYield 56.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To the solution of 1-methyl-1H-imidazole (2 g, 24.4 mmol) in 16 mL of DCM was added dropwise 4.4 g of trichloroacetyl chloride and the resulting mixture was stirred at 25° C. for 6 h. The mixture was cooled to 0° C. and 3.4 mL of triethylamine was added dropwise with stirring. The solvent was evaporated and the residue was purified by flash column chromatography (petroleum ether/DCM=4/1) to give 2,2,2-trichloro-1-(1-methyl-1H-imidazol-2-yl)ethanone (3.1 g, yield 56%). 1H NMR (300 MHz, CDCl3) δ 7.35 (s, 1H), 7.16 (s, 1H), 4.06 (s, 3H).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringwith stirring
  3. customThe solvent was evaporated
  4. customthe residue was purified by flash column chromatography (petroleum ether/DCM=4/1)

Sources & evidence

ORD record
ord-ad68acdf6197480689bec94cf130078d
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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