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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1399839Generated: October 29, 2026

p-Toluenesulfonic acid monohydrate → 1-benzyl-6-bromo-1H-benzo[d]imidazole

https://huagongshe.com/reaction/1399839

Reaction equation

Participants

RoleNameHCIDCharge
Reactantp-Toluenesulfonic acid monohydrateHCID 521998—
ReactantN1-benzyl-5-bromobenzene-1,2-diamineHCID 65343042—
SolventTrimethyl orthoformateHCID 9005—
Product1-benzyl-6-bromo-1H-benzo[d]imidazoleHCID 86729250—

Reaction Conditions

Temperature100 °C

Reaction Steps

To a solution of N1-benzyl-5-bromobenzene-1,2-diamine (450 mg, 1.63 mmol) in HC(OMe)3 (15 mL) was added TsOH.H2O (30 mg, 0.16 mmol). The mixture was stirred at 100° C. for 4 h. The reaction solution was concentrated, and the residue was washed with water and extracted with EtOAc. The organic layer was concentrated to give the crude 1-benzyl-6-bromo-1H-benzo[d]imidazole. The crude product was used in next step without further purification. LCMS (m/z): 287.1/288.1 [M+H]+/[M+2H]+

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08906900B2
Source datasetuspto-grants-2014_12
ORD IDord-3d1269d722b148eabfafcf2ffa0b7d55
Source noteuspto-grants-2014_12