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

HRID 375194

반응식

HRID 375194 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 mL) 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°-164.0° 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-e21a252a88244b3a9d0b69f9180d2ee6
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05484807

연결된 노트

불러오는 중…