Triethylamine → N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide

HRID 499997노트

반응식

HRID 499997 반응식
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[Cl:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([F:20])[C:11]=1[O:21][C:22]1[CH:26]=[C:25]([CH3:27])[NH:24][N:23]=1.[CH2:28]([NH2:34])[CH:29]1[O:33][CH2:32][CH2:31][CH2:30]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:28]([NH:34][C:2]([N:24]1[C:25]([CH3:27])=[CH:26][C:22]([O:21][C:11]2[C:12]([F:20])=[CH:13][C:14]([C:16]([F:19])([F:17])[F:18])=[CH:15][C:10]=2[Cl:9])=[N:23]1)=[O:3])[CH:29]1[O:33][CH2:32][CH2:31][CH2:30]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 253298TetrahydrofurfurylamineHCID 178624283-(2-Chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole

생성물 1

HCID 17862429N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide수율 29.6%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

Trichloromethyl chloroformate (0.39 g, 2.0 mmol) was added to a chloroform (10 mL) solution of 3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole (0.59 g, 2.0 mmol) at 0° C., and while the mixture was allowed to gradually warm up to a room temperature, it was further stirred at room temperature for 3 hours. Tetrahydrofurfurylamine (0.61 g, 6.0 mmol) and triethylamine (0.4 g, 4.0 mmol) were added to the reaction mixture, and the mixture was refluxed under heating for 5 hours. After completion of the reaction, the reaction mixture was poured into ice and extracted with chloroform (20 mL×3 times). The organic layer was washed with water and dried over anhydrous magnesium sulfate, the desiccant was removed by filtering, and the solvent was distilled off the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate/hexane= 1/10˜⅕) to give a colorless viscous substance of N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (0.25 g, yield: 29.6%). 1H-NMR (CDCl3, TMS, ppm): δ1.50-1.65 (m, 1H), 1.75˜2.05 (m, 3H), 2.58 (s, 3H), 3.32 (dt, J=6.3 and 13.9 Hz, 1H), 3.48 (ddd, J=3.7, 5.7 and 13.9 Hz, 1H), 3.74 (dq, J=7.0 and 8.6 Hz, 2H), 4.03 (dq, J=3.7 and 7.0 Hz, 1H), 5.79 (s, 1H), 6.85˜7.10 (m, 1H), 7.39 (dd, J=1.9 and JHF=9.3 Hz, 1H), 7.56 (s, 1H).

후처리

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 5 hours
  3. customAfter completion of the reaction
  4. additionthe reaction mixture was poured into ice
  5. extractionextracted with chloroform (20 mL×3 times)
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe desiccant was removed
  9. filtrationby filtering
  10. distillationthe solvent was distilled off the filtrate under reduced pressure
  11. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane= 1/10˜⅕)

출처 및 근거

ORD 기록
ord-c28b1aa26c74445aa859a5d2e26e2a02
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767827B2

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