Methyl chloroformate → HCID 19919342, compound

HRID 1648309Notes

Reaction equation

HRID 1648309 reaction equation
[H-].[K+].[Cl:3][C:4]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([CH3:13])[C:6]=2[N:5]=1.Cl[C:15]([O:17][CH3:18])=[O:16]>C1COCC1>[Cl:3][C:4]1[N:8]([C:15]([O:17][CH3:18])=[O:16])[C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([CH3:13])[C:6]=2[N:5]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 82127Potassium hydrideHCID 149330232-Chloro-4-methyl-1H-benzimidazole

Product 1

HCID 19919342HCID 19919342, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium hydride (0.85 g of 35% in oil, washed with ether to remove oil, 7.4 mmol) was added to a stirred solution of 2-chloro-4-methyl-1H-benzimidazole (1.23 g, 7.4 mmol) in THF (25 mL). Methyl chloroformate (0.7 g, 7.4 mmol) was added and the reaction was stirred 10 minutes. The solvent was removed and the material was partitioned between ethyl acetate and water. Evaporation of the organic layer gave 1.68 g of white solid. Crystallization from hexane gave 1.42 g of white crystals, mp 90°-91° C. Anal. Calc'd for C10H9ClN2O2 : C, 53.47; H, 4.04; C1, 15.78; N, 12.47. Found: C, 53.63; H, 4.11; Cl, 15.81; N, 12.45.

Workup

  1. customThe solvent was removed
  2. customthe material was partitioned between ethyl acetate and water
  3. customEvaporation of the organic layer

Sources & evidence

ORD record
ord-b8fd7edac42140448debf0b659e7f894
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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