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

HRID 894020Notes

Reaction equation

HRID 894020 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-f24e3a242b6949398a3128ee0776f74f
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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