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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1048963Generated: November 1, 2026

1,1'-Carbonyldiimidazole → 1-cyclopropyl-5,6-difluoro-1H-benzo[d]imidazol-2(3H)-one

https://huagongshe.com/reaction/1048963

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,1'-CarbonyldiimidazoleHCID 68263—
ReactantN1-cyclopropyl-4,5-difluorobenzene-1,2-diamineHCID 68053726—
SolventTetrahydrofuranHCID 8028—
SolventEthyl AcetateHCID 8857—
Product1-cyclopropyl-5,6-difluoro-1H-benzo[d]imidazol-2(3H)-oneHCID 6669355268.5%

Reaction Steps

Carbonyldiimidazole (4.3 g) was added to the solution of N1-cyclopropyl-4,5-difluorobenzene-1,2-diamine (3.2 g) in THF (30 ml). The mixture was stirred at rt for 20 hours, then diluted with ethyl acetate (200 ml) and washed with hydrochloric acid (1M, 200 ml). Organic layer dried over sodium sulphate, solvent removed to give expected product as a black solid (2.5 g). 1H NMR (CD3OD)δ: 7.20 (dd, 1H), 6.95 (dd, 1H), 2.86 (m, 1H), 1.11 (m, 2H), 0.94 (m, 2H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09382226B2
Source datasetuspto-grants-2016_07
ORD IDord-471d23be7c0c49198a882315f7189648
Source noteuspto-grants-2016_07