Chloroacetic Acid → 2-Chloromethylbenzimidazole

HRID 273759Notes

Reaction equation

HRID 273759 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].Cl.[Cl:10][CH2:11][C:12](O)=O>O.O.N>[Cl:10][CH2:11][C:12]1[NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[N:8]=1

Participants

6

Reactant 3

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 7243O-Phenylenediamine

Product 1

HCID 785712-ChloromethylbenzimidazoleYield 67.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12896473Azane;hydrateSolvent

Procedure

To 108 g of o-phenylenediamine, 1 l of 4N hydrochloric acid and 142 g of chloroacetic acid were added and refluxed for 1.5 hours. After allowing to stand overnight, the solution was diluted with 2 l of water and neutralized with dilute ammonia water. The formed crystals were filtered off to obtain 113 g of 2-chlorom ethylbenzimidazole.

Workup

  1. temperaturerefluxed for 1.5 hours
  2. filtrationThe formed crystals were filtered off

Sources & evidence

ORD record
ord-8aea802ad77c4e789d283f5203dc4688
Source dataset
uspto-grants-1995_02
Patent number
US05387600

Reaction notes

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