O-Toluidine → HCID 858984, compound

Participants

Reaction Steps

A solution of triphosgene (1.469 g, 4.95 mmol) in chloroform (10 ml) was added dropwise with a solution of 1-methylpiperazine (1.5 g, 15 mmol) in chloroform (10 ml) with stirring under ice cooling, and the mixture was stirred at room temperature for one hour. The resulting suspension of acid chloride was added dropwise with a solution of ortho-toluidine (1.071 g, 10 mmol) in chloroform (10 ml), and added with triethylamine (1.518 g, 15 mmol), and the mixture was refluxed for 12 hours. The reaction mixture was added to water to precipitate a diphenyl urea derivative, which was separated by filtration. Then, the aqueous layer was made sufficiently acidic with 10% hydrochloric acid and washed with dichloromethane. The aqueous layer was made sufficiently basic with 20% aqueous potassium carbonate and extracted with dichloromethane. The organic layer washed with a small volume of water and dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The resulting mixture was recrystallized from ethyl acetate/n-hexane to obtain colorless acicular crystals. Melting point: 148-149° C.

Provenance & Evidence