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

HRID 1980890Notes

Reaction equation

HRID 1980890 reaction equation
[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

Participants

3

Reactant 2

HCID 10154307m-Chlorobenzenesulfenyl chlorideHCID 12361759methyl 1H-pyrrole-3-carboxylate

Product 1

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

Procedure

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.

Sources & evidence

ORD record
ord-1c9f1b42061c459e9b89ff59cc9eb07f
Source dataset
uspto-grants-1985_04
Patent number
US04511575

Reaction notes

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