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Hydrochloric Acid → N-methoxymethyl-3-(4-cyano-2-trifluoromethylphenyloxy)-5-methylpyrazole-1-carbothioamide

HRID 644895
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HRID 644895 반응식
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][CH2:9][N:10]=[C:11]=[S:12].[C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:26]=[C:25]([CH3:27])[NH:24][N:23]=2)=[C:17]([C:28]([F:31])([F:30])[F:29])[CH:16]=1)#[N:14].Cl>C(OCC)(=O)C>[CH3:7][O:8][CH2:9][NH:10][C:11]([N:24]1[C:25]([CH3:27])=[CH:26][C:22]([O:21][C:18]2[CH:19]=[CH:20][C:15]([C:13]#[N:14])=[CH:16][C:17]=2[C:28]([F:29])([F:30])[F:31])=[N:23]1)=[S:12]
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 140624Methoxymethyl isothiocyanateHCID 178623343-(4-Cyano-2-trifluoromethylphenyloxy)-5-methylpyrazole

생성물 1

HCID 17862473N-methoxymethyl-3-(4-cyano-2-trifluoromethylphenyloxy)-5-methylpyrazole-1-carbothioamide수율 32.4%

시약·촉매·용매 1

HCID 8857
Ethyl Acetate
용매

실험 절차

Potassium carbonate (0.23 g, 1.7 mmol) and methoxymethyl isothiocyanate (0.15 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 white solid of N-methoxymethyl-3-(4-cyano-2-trifluoromethylphenyloxy)-5-methylpyrazole-1-carbothioamide (0.18 g, yield: 32.4%) mp: 89-90° C.; 1H-NMR (CDCl3, TMS, ppm): δ 2.84 (s, 3H), 3.44 (s, 3H), 5.13 (d, J=6.2 Hz, 2H), 5.98 (m, 1H), 7.44 (d, J=8.7 Hz, 1H), 7.84 (dd, J=2.0 and 8.7 Hz, 1H), 8.01 (d, J=2.0 Hz, 1H), 8.95-9.30 (m, 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-c5880e167f0a426a8ac8bad77878668a
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07700786B2

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