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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2386782Generated: October 31, 2026

Methanol → 5-Bromo-1,3-dihydro-2H-benzimidazol-2-one

https://huagongshe.com/reaction/2386782

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantWaterHCID 962—
Reactant1,1'-CarbonyldiimidazoleHCID 68263—
Reactant4-Bromobenzene-1,2-diamineHCID 323593—
SolventN-methyl-2-pyrrolidoneHCID 13387—
Product5-Bromo-1,3-dihydro-2H-benzimidazol-2-oneHCID 12228060—

Reaction Conditions

Temperature100 °C

Reaction Steps

1,1′-Carbonyldiimidazole (2.1 g) in NMP (5 ml) was added to a solution of 4-bromo-o-phenylenediamine (CAS Reg. No. 1575-37-7, 2 g) in NMP (5 ml). The mixture was heated to 100° C. for 2 h and then allowed to cool to 60° C. MeOH (3 ml) was added, and the mixture was allowed to cool to room temperature. Water (50 ml) was added. The mixture was filtered. The residue was washed with isopropanol and then dried in vacuo to give the title compound (1.65 g) as a dark brown solid. MS (m/e, ISP neg. ion)=213.1 [M−H+].

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08268820B2
Source datasetuspto-grants-2012_09
ORD IDord-0e6244d71b8141d889592a2c8326bc5f
Source noteuspto-grants-2012_09