Methanesulfenyl chloride, trifluoro- → Ethyl 4-(p-chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole-3-carboxylate

HRID 1464670

반응식

HRID 1464670 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][NH:11][CH:12]=2)=[CH:4][CH:3]=1.[F:18][C:19]([F:23])([F:22])[S:20]Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][NH:11][C:12]=2[S:20][C:19]([F:23])([F:22])[F:18])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 67900Methanesulfenyl chloride, trifluoro-2회HCID 470434ethyl 4-(4-chlorophenyl)-1H-pyrrole-3-carboxylate

생성물 1

HCID 18930389Ethyl 4-(p-chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole-3-carboxylate수율 95.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-30 °C

실험 절차

A solution of ethyl 4-(p-chlorophenyl)pyrrole-3-carboxylate (9.0 g, 0.036 mol) in methylene chloride (180 mi) is treated with trifluoromethylsulfenyl chloride (4.9 g, 0.036 mol) with stirring for 45 minutes at -30° C. The reaction mixture is warmed to room temperature and stirred for several hours. Since a TLC shows some starting material present, the reaction mixture is cooled to -30° C., treated with additional trifluoromethylsulfenyl chloride (1.3 g, 0.0095 mol), warmed to room temperature overnight with stirring, washed with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title product as an off-white solid (12.0 g, mp 161.5°-164.00° C.) which is identified by 1HNMR, 19FNMR and 13CNMR spectral analyses.

후처리

  1. temperatureThe reaction mixture is warmed to room temperature
  2. stirringstirred for several hours
  3. temperaturethe reaction mixture is cooled to -30° C.
  4. temperaturewarmed to room temperature overnight
  5. stirringwith stirring
  6. washwashed with water, saturated sodium hydrogen carbonate solution and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-dd9f1e78590346f9a21494eb23d5a77f
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05306827

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