Ethyl bromoacetate → 1-Ethoxycarbonylmethyl-3-phenyl-benzimidazolium bromide

HRID 26702Notes

Reaction equation

[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>>[Br-:16].[CH2:21]([O:20][C:18]([CH2:17][N+:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=1)=[O:19])[CH3:22]

Participants

Reactant 2

HCID 7748Ethyl bromoacetate

HCID 6066691-Phenyl-1H-benzoimidazole

Product 1

HCID 140675511-Ethoxycarbonylmethyl-3-phenyl-benzimidazolium bromideYield 56%

Procedure

Using the procedure of Step B of Example 1, 1-phenylbenzimidazole [prepared from N-phenyl-o-phenylenediamine with 4HCl and formic acid] and ethyl bromoacetate were reacted to obtain a 56% of 1-ethoxycarbonylmethyl-3-phenyl-benzimidazolium bromide which after crystallization from a mixture of ethyl acetate and methanol melted at 180°-181° C.

Workup

customwere reacted

Sources & evidence

ORD record: ord-884eb9d0373d47e7aacf2db69e72e913
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04151280

Reaction notes

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