Ammonia → HCID 17862448, compound

Trichloromethyl chloroformate (3.0 g, 15.0 mmol) was added to a solution of 3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole (4.67 g, 15.0 mmol) in chloroform (50 ml) at 0° C., and while the mixture was allowed to have room temperature gradually, it was further stirred at room temperature for 4 hours. 30% ammonia solution (10 ml) was added to the reaction mixture, and the mixture was further stirred at room temperature for 1 hour. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (30 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 white solid of 3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (2.82 g, yield: 53.1%). mp: 152-154° C.; 1H-NMR (CDCl3, TMS, ppm): δ 2.58 (d, J=0.4 Hz, 3H), 4.80-5.15 (br s, 1H), 5.80 (q, J=0.4 Hz, 1H), 6.45-6.80 (br s, 1H), 7.66 (s, 2H).

1. customto have room temperature
2. stirringthe mixture was further stirred at room temperature for 1 hour
3. additionwas added to the reaction mixture
4. extractionthe mixture was extracted with ethyl acetate (30 ml×3)
5. washAn organic layer was washed with water
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. customto remove a desiccant, and the solvent
9. distillationwas distilled off from the filtrate under reduced pressure
10. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/7)

ORD record

ord-85ae30419ae34003b158796b9530e6cf

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07700786B2