methyl 1H-pyrrole-3-carboxylate → Methyl 5-(4-chlorophenylthio)pyrrole-3-carboxylate

HRID 1703253노트

반응식

HRID 1703253 반응식
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[CH:2]1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]Cl)=[CH:13][CH:12]=1.C(Cl)Cl>CCOCC>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([S:17][C:5]2[NH:1][CH:2]=[C:3]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=2)=[CH:13][CH:12]=1

참가 물질

4

반응물 2

HCID 12361759methyl 1H-pyrrole-3-carboxylateHCID 20523678HCID 20523678, 화합물

생성물 1

HCID 12897034Methyl 5-(4-chlorophenylthio)pyrrole-3-carboxylate수율 26.1%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

Methyl pyrrole-3-carboxylate (2.5 g., 20 mmole) was dissolved in 35 ml. of methylene chloride p-Chlorobenzenesulfenyl chloride (4.0 g., 22 mmoles) was added dropwise over approximately 2 minutes, and the reaction mixture was stirred at room temperature for 1 hour. Two volumes of ether were added, the mixture extracted twice with 20 ml. portions of water and the organic layer evaporated in vacuo. The resulting oil was chromatographed on 100 g. of silica gel with approximately 25 ml. fractions of the ethyl acetate-1/hexane-7 eluant collected. Fractions 19 to 36 were combined and concentrated to yield methyl 5-(4-chlorophenylthio)pyrrole-3-carboxylate (1.4 g., m.p. 122°-124° C.).

후처리

  1. extractionthe mixture extracted twice with 20 ml
  2. customportions of water and the organic layer evaporated in vacuo
  3. customThe resulting oil was chromatographed on 100 g
  4. customfractions of the ethyl acetate-1/hexane-7 eluant collected
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-94d68ddc730c4e41875af506340de2b7
출처 데이터셋
uspto-grants-1982_09
특허 번호
US04351843

반응 노트

불러오는 중…