p-Toluenesulfenyl chloride → Methyl 5-(4-methylphenylthio)pyrrole-3-carboxylate

HRID 894017노트

반응식

HRID 894017 반응식
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[CH:2]1.[C:10]1([CH3:18])[CH:15]=[CH:14][C:13]([S:16]Cl)=[CH:12][CH:11]=1>C(Cl)Cl>[CH3:18][C:10]1[CH:15]=[CH:14][C:13]([S:16][C:5]2[NH:1][CH:2]=[C:3]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=2)=[CH:12][CH:11]=1

참가 물질

4

반응물 2

HCID 11019146p-Toluenesulfenyl chlorideHCID 12361759methyl 1H-pyrrole-3-carboxylate

생성물 1

HCID 12897028Methyl 5-(4-methylphenylthio)pyrrole-3-carboxylate수율 28.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Methyl pyrrole-3-carboxylate (2.5 g., 20 mmoles) was dissolved in 50 ml. of methylene chloride. To the stirred solution there was added dropwise p-toluenesulfenyl chloride (2.92 g., 20 mmoles), with the temperature maintained below 30° C. by occasional cooling with an ice-water bath. The reaction was stirred for 60 minutes at room temperature. The reaction mixture was concentrated in vacuo to an oil. The residue was taken up in a mixture of isopropyl alcohol and hexane, a small amount of gum removed by filtration and the filtrate evaporated in vacuo to an oil (5.0 g.). The latter was chromatographed on 150 g. of silica gel, with 100 ml. fractions of the benzene eluant collected. Fractions 10 to 19 were combined to yield the desired product (1.41 g.) contaminated with an impurity showing a mass spectral peak at 281. The latter was removed by recrystallization from methylene chloride/hexane to yield purified methyl 5-(4-methylphenylthio)pyrrole-3-carboxylate (1.14 g., m.p. 118°-121° C., m/e 247).

후처리

  1. temperaturewith the temperature maintained below 30° C.
  2. temperatureby occasional cooling with an ice-water bath
  3. concentrationThe reaction mixture was concentrated in vacuo to an oil
  4. additionThe residue was taken up in a mixture of isopropyl alcohol and hexane
  5. customa small amount of gum removed by filtration
  6. customthe filtrate evaporated in vacuo to an oil (5.0 g.)
  7. customThe latter was chromatographed on 150 g
  8. customfractions of the benzene eluant collected

출처 및 근거

ORD 기록
ord-33ea27b49f2b4ec8b269aa9731d3217c
출처 데이터셋
uspto-grants-1981_08
특허 번호
US04282242

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