Hydrochloric Acid → N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carbothioamide

HRID 644897노트

반응식

HRID 644897 반응식
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([N:9]=[C:10]=[S:11])[CH3:8].[Cl:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([F:23])[C:14]=1[O:24][C:25]1[CH:29]=[C:28]([CH3:30])[NH:27][N:26]=1.Cl>C(OCC)(=O)C>[CH2:7]([NH:9][C:10]([N:27]1[C:28]([CH3:30])=[CH:29][C:25]([O:24][C:14]2[C:15]([F:23])=[CH:16][C:17]([C:19]([F:22])([F:20])[F:21])=[CH:18][C:13]=2[Cl:12])=[N:26]1)=[S:11])[CH3:8]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 10966Ethyl isothiocyanateHCID 11430Potassium CarbonateHCID 178624283-(2-Chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole

생성물 1

HCID 17862390N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carbothioamide수율 9.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Potassium carbonate (0.22 g, 1.6 mmol) and ethyl isothiocyanate (0.13 g, 1.8 mmol) were added to a solution of 3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole (0.44 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 white solid of N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carbothioamide (0.05 g, yield: 9.4%). mp: 114-115° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.25 (t, J=7.3 Hz, 3H), 2.81 (d, J=0.6 Hz, 3H), 3.67 (dq, J=5.7 and 7.3 Hz, 2H), 5.84 (q, J=0.6 Hz, 1H), 7.41 (dd, JHF=2.1 and 9.4 Hz, 1H), 7.62 (s, 1H), 8.54 (br s, 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-7e79aa6df1294f44be847ee75cae9f9d
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700786B2

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