Hydrochloric Acid → N-ethyl-3-(4-cyano-2-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide

HRID 644858노트

반응식

HRID 644858 반응식
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([N:9]=[C:10]=[O:11])[CH3:8].[C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=2)=[C:16]([C:27]([F:30])([F:29])[F:28])[CH:15]=1)#[N:13].Cl>C(OCC)(=O)C>[CH2:7]([NH:9][C:10]([N:23]1[C:24]([CH3:26])=[CH:25][C:21]([O:20][C:17]2[CH:18]=[CH:19][C:14]([C:12]#[N:13])=[CH:15][C:16]=2[C:27]([F:28])([F:29])[F:30])=[N:22]1)=[O:11])[CH3:8]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 11430Potassium CarbonateHCID 178623343-(4-Cyano-2-trifluoromethylphenyloxy)-5-methylpyrazole

생성물 1

HCID 17862352N-ethyl-3-(4-cyano-2-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide수율 69%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Potassium carbonate (0.23 g, 1.7 mmol) and ethyl isocyanate (0.11 g, 1.5 mmol) were added to a solution of 3-(4-cyano-2-trifluoromethylphenyloxy)-5-methylpyrazole (0.40 g, 1.5 mmol) in ethyl acetate (10 ml), and the mixture was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate (10 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=1/10), to give a yellowish solid of N-ethyl-3-(4-cyano-2-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (0.35 g, yield: 69.0%). mp: 103-105° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.23 (t, J=7.3 Hz, 3H), 2.63 (d, J=0.7 Hz, 3H), 3.39 (dq, J=5.9 and 7.2 Hz, 2H), 5.85 (q, J=0.7 Hz, 1H), 6.80-7.00 (m, 1H), 7.38 (d, J=8.7 Hz, 1H), 7.81 (dd, J=1.8 and 8.7 Hz, 1H), 7.99 (d, J=1.8 Hz, 1H).

후처리

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

출처 및 근거

ORD 기록
ord-3c5aa67770e545a892230aac9eaeeaa5
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700786B2

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