O-Toluidine → HCID 858984, compound

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.

1. stirringthe mixture was stirred at room temperature for one hour
2. temperaturethe mixture was refluxed for 12 hours
3. customto precipitate a diphenyl urea derivative, which
4. customwas separated by filtration
5. washwashed with dichloromethane
6. extractionextracted with dichloromethane
7. washThe organic layer washed with a small volume of water
8. dry with materialdried over anhydrous sodium sulfate
9. customthe solvent was evaporated under reduced pressure
10. customThe resulting mixture was recrystallized from ethyl acetate/n-hexane
11. customto obtain colorless acicular crystals

ORD record

ord-294dc2228c6e43b294f8f6b701c6f2ae

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07485646B2