Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2262425Generated: October 28, 2026

Benzoic Acid → 4-Bromo-N-(2-(phenylamino)phenyl)benzamide

https://huagongshe.com/reaction/2262425

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzoic AcidHCID 243—
Reactant4-Bromobenzoic acidHCID 11464—
ReactantThionyl ChlorideHCID 24386—
ReactantN-Phenyl-o-phenylenediamineHCID 68297—
CatalystDimethylformamideHCID 6228—
Solvent1,2-DichloroethaneHCID 11—
SolventWaterHCID 962—
Product4-Bromo-N-(2-(phenylamino)phenyl)benzamideHCID 2309405594.4%

Reaction Steps

Suspending 3.0 g (15 mmol) of 4-bromobenzoic acid into 30 milliliter of 1,2-dichloroethane, adding 2.7 g (23 mmol) of thionyl chloride and 3 drops of N,N-dimethylformamide, the resultant solution was stirred with heating at the temperature of about 50° C. for 1 hour and 30 minutes until benzoic acid as the material disappeared. After completion of the reaction, removing the solvent and excess thionyl chloride by distillation, dissolving the resultant acid chloride into 30 milliliter of N-methylpyrrolidone, adding 2.8 g (15 mmol) of N-phenyl-1,2-phenylenediamine, the resultant solution was stirred at room temperature for a night. After completion of the reaction, adding water and filtering the precipitated solid, further washing with water and by drying under reduced pressure, 5.2 g of 4-bromo-N-(2-phenylamino-phenyl)-benzamide was obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07851071B2
Source datasetuspto-grants-2010_12
ORD IDord-f6cffc21e0994c5c811ed1e959e055e5
Source noteuspto-grants-2010_12