m-Chlorobenzenesulfenyl chloride → Methyl 5-(3-Chlorophenylthio)pyrrole-3-carboxylate

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

참가 물질

반응물 2

HCID 10154307m-Chlorobenzenesulfenyl chloride

HCID 12361759methyl 1H-pyrrole-3-carboxylate

생성물 1

HCID 12897032Methyl 5-(3-Chlorophenylthio)pyrrole-3-carboxylate

실험 절차

By the procedure of Example 14, methyl pyrrole-3-carboxylate (2.5 g., 20 mmoles) was reacted with m-chlorobenzenesulfenyl chloride to yield crude product as an oil (5.0 g.). The crude was chromatographed on 250 g. of silica gel, with 100 ml. fractions of the methylene chloride eluant collected. Fractions 17 to 30 were combined and evaporated to yield purified methyl 5-(3-chlorophenylthio)pyrrole-3-carboxylate (1.8 g., m.p. 90°-95° C., m/e 267) which crystallized on standing.

출처 및 근거

ORD 기록: ord-0e29b3d41343454495b089df92c4edfe
출처 데이터셋: uspto-grants-1982_09
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US04351843

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