O-Toluidine → HCID 4406746, compound

Participants

Reaction Steps

To a stirred solution of 42.8 parts of 2-methylbenzenamine in 375 parts of trichloromethane are added dropwise 41.8 parts of 2,6-dichlorobenzoyl chloride at reflux temperature. Then there are added 1.2 parts of N,N-dimethyl-4-pyridinamine and stirring is continued for 3 hours at reflux. The reaction mixture is allowed to cool to room temperature overnight and diluted with 375 parts of trichloromethane. The organic phase is washed successively with 100 parts of water, 100 parts of a hydrochloric acid solution 3 N and again 100 parts of water, dried, filtered and evaporated. The residue is crystallized from 200 parts of 2-propanol, yielding 40.6 parts (72.5%) 2,6-dichloro-N-(2-methylphenyl)benzamide; mp. 182.5° C.

Provenance & Evidence