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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2112822Generated: October 31, 2026

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

https://huagongshe.com/reaction/2112822

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,1'-CarbonyldiimidazoleHCID 68263—
Reactant4-Bromobenzene-1,2-diamineHCID 323593—
SolventDimethylformamideHCID 6228—
Product5-Bromo-1,3-dihydro-2H-benzimidazol-2-oneHCID 12228060—

Reaction Conditions

Temperature80 °C

Reaction Steps

4.29 g (26.46 mmol) of carbonyldiimidazole (CDI) is added to a solution of 4.5 g (24.05 mmol) of 4-bromobenzene-1,2-diamine in 95 mL of DMF and the reaction mixture is stirred for 5 hours at 80° C. Then the reaction mixture is poured onto water and the precipitate formed is filtered off. The precipitate is washed three times with water and dried in the circulating air dryer at 60° C. Yield: 4.6 g (90% of theoretical); C7H5BrN2O (M=213.03); calc.: molpeak (M+H)+: 213/215; found: molpeak(M+H)+: 213/215; Rf value: 0.5 (silica gel, DCM/MeOH 10:1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07524862B2
Source datasetuspto-grants-2009_04
ORD IDord-57cae01db86643fc80de27d9654d7aec
Source noteuspto-grants-2009_04