Diphosgene → HCID 17862380, compound

Trichloromethyl chloroformate (0.59 g, 3.0 mmol) was added to a solution of 3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole (0.83 g, 3.0 mmol) in chloroform (10 ml) at 0° C., and while the mixture was allowed to have room temperature gradually, it was further stirred at room temperature for 3 hours. Cyclopropylamine (0.17 g, 3.0 mmol) and potassium carbonate (0.50 g, 3.6 mmol) were added to the reaction mixture, and the reaction mixture was refluxed under heating for 5 hours. After completion of the reaction, the reaction mixture was poured into ice water and extracted with chloroform (20 ml×3). An organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered to remove a desiccant, and the solvent was distilled off from the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/7), to give a colorless viscous substance of N-cyclopropyl-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (0.27 g, yield: 22.8%). 1H-NMR (CDCl3, TMS, ppm): δ 0.55-0.65 (m, 2H), 0.75-0.85 (m, 2H), 2.59 (d, J=0.4 Hz, 3H), 2.60-2.75 (m, 1H), 5.71 (m, 1H), 6.75-6.90 (m, 1H), 7.67 (s, 2H).

1. customto have room temperature
2. temperaturethe reaction mixture was refluxed
3. temperatureunder heating for 5 hours
4. customAfter completion of the reaction
5. extractionextracted with chloroform (20 ml×3)
6. washAn organic layer was washed with water
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. customto remove a desiccant, and the solvent
10. distillationwas distilled off from the filtrate under reduced pressure
11. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/7)

ORD record

ord-db3018d8aec34bbd974735a5c9ed3e9b

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07700786B2