1,2-Dichloroethane → 2-(p-Chlorophenyl)-3-[(trifluoromethyl)sulfonyl]-5-[(trifluoromethyl)thio]pyrrole

HRID 1975208노트

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HRID 1975208 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[CH:11][C:12]=2[S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])=[CH:4][CH:3]=1.[F:20][C:21]([F:25])([F:24])[S:22]Cl.FC(F)(F)S(O)(=O)=O.ClCCCl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10]([S:22][C:21]([F:25])([F:24])[F:20])=[CH:11][C:12]=2[S:13]([C:16]([F:17])([F:19])[F:18])(=[O:14])=[O:15])=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 62406Trifluoromethanesulfonic acidHCID 67900Methanesulfenyl chloride, trifluoro-HCID 10448068HCID 10448068, 화합물

생성물 1

HCID 189304062-(p-Chlorophenyl)-3-[(trifluoromethyl)sulfonyl]-5-[(trifluoromethyl)thio]pyrrole수율 72%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
70 °C

실험 절차

A solution of 2-(p-chlorophenyl)-3-[(trifluoromethyl)sulfonyl]pyrrole (2.47 g, 0.0080 mol), trifluoromethylsulfenyl chloride (2.18 g, 0.016 mol), trifluoromethanesulfonic acid (0.12 g, 0.0008 mol) and 1,2-dichloroethane (15 mL) is placed in a pressure tube, heated at 70° C. for five days, diluted with methylene chloride, washed with saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain an amber syrup. Flash chromatography of the syrup using silica gel and a 1:5 ethyl acetate/hexanes solution gives the title product as an off-white solid (2.36 g, mp 118°-122° C.) which is identified by 1HNMR and 13CNMR spectral analyses.

후처리

  1. washwashed with saturated sodium hydrogen carbonate solution and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto obtain an amber syrup

출처 및 근거

ORD 기록
ord-54142b4b8e154dbb8c92c1b70a9d17f9
출처 데이터셋
uspto-grants-1994_02
특허 번호
US05284863

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