Bromo(phenyl)acetic acid → HCID 4235566, compound

HRID 463543Notes

Reaction equation

HRID 463543 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Br[CH:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13]([OH:15])=[O:14]>CC(C)=O>[NH:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[S:1][CH:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 97919Bromo(phenyl)acetic acidHCID 178527775HCID 178527775, compound

Product 1

HCID 4235566HCID 4235566, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

An acetone solution of 13.5 g (0.09M) of 2-mercaptobenzimidazole and 19.4 g (0.09M) of α-bromophenylacetic acid containing 10 ml glacial acetic acid is heated for 3 hours. The solid HBr salt upon removal of the solvent is disproportionated by stirring in 1 L of water. The crude material is recrystallied from aqueous acetone. The recrystallized material weighs 24.0 g (92% yield) and melts at 187°-8° C. dec.

Workup

  1. customThe solid HBr salt upon removal of the solvent

Sources & evidence

ORD record
ord-e02076fc991e49829f4238a7d43a9b14
Source dataset
uspto-grants-1985_05
Patent number
US04520196

Reaction notes

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