4-Fluorophenylhydrazine hydrochloride → 5-[3,5-difluoro-4-(methylthio)-phenyl]-1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole

HRID 47640

반응식

HRID 47640 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:11](=O)[CH2:12][C:13](=O)[C:14]([F:17])([F:16])[F:15])[CH:5]=[C:6]([F:10])[C:7]=1[S:8][CH3:9].Cl.[F:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][NH2:29])=[CH:24][CH:23]=1>C(O)C.Cl>[F:1][C:2]1[CH:3]=[C:4]([C:11]2[N:28]([C:25]3[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=3)[N:29]=[C:13]([C:14]([F:17])([F:16])[F:15])[CH:12]=2)[CH:5]=[C:6]([F:10])[C:7]=1[S:8][CH3:9]

참가 물질

5

반응물 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 227465181-[3,5-Difluoro-4-(methylthio)phenyl]-4,4,4-trifluorobutane-1,3-dione

생성물 1

HCID 227457735-[3,5-difluoro-4-(methylthio)-phenyl]-1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 702Ethanol용매

실험 절차

1-[3,5-difluoro-4-(methylthio)phenyl]-4,4,4-trifluoro-butane-1,3-dione (1.09 g, 3.6 mmol) dissolved in ethanol (150 mL). One drop of concentrated hydrochloric acid was added and 4-fluorophenylhydrazine hydrochloride (0.69 g, 4.0 mmol). The reaction was stirred at ambient temperature for 72 hours. Solvent was removed in vacuo and the residue was dissolved in ethyl acetate (100 mL) extracted with water (2×100 mL), saturated ammonium chloride (2×150 mL) and dried over sodium sulfate. The solvent was removed in vacuo and the 5-[3,5-difluoro-4-(methylthio)-phenyl]-1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole was obtained by crystallization from ethyl acetate and hexanes (0.71 g, 50%). 1H NMR (CDCl3/300 MHz) 7.36-7.29 (m, 2H), 7.18-7.13 (m, 2H), 6.81-6.77 (m, 3H), 2.53 (s, 3H). ESHRMS m/z 389.0557 (M+H+, Calcd 389.0547). Anal. Calcd for C17H10F6N2S: C, 52.58; H, 2.34; N, 7.21. Found: C, 52.45; H, 2.34; N, 7.15.

후처리

  1. customSolvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  3. extractionextracted with water (2×100 mL), saturated ammonium chloride (2×150 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-21b63af5b6244e409b98f59fb8f2f543
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699884B2

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