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

HRID 894029Notes

Reaction equation

HRID 894029 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:18]Cl)[CH:14]=[CH:15][C:16]=1[Cl:17]>>[Cl:10][C:11]1[CH:12]=[C:13]([S:18][C:5]2[NH:1][CH:2]=[C:3]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=2)[CH:14]=[CH:15][C:16]=1[Cl:17]

Participants

3

Reactant 2

HCID 12361759methyl 1H-pyrrole-3-carboxylateHCID 128785403,4-Dichlorobenzenesulfenyl chloride

Product 1

HCID 12897048Methyl 5-(3,4-Dichlorophenylthio)pyrrole-3-carboxylateYield 104.2%

Procedure

By the procedure of Example 23, methyl pyrrole-3-carboxylate (2.5 g., 20 mmoles) was reacted with 3,4-dichlorobenzenesulfenyl chloride (4.24 g., 20 mmoles) to yield crude product (6.3 g., oil). The crude was chromatographed on 250 g. of silica gel, with 125 ml. fractions of the ethyl acetate-1/hexane-5/5% acetic acid eluant collected. Fractions 2 to 6 were combined and evaporated to dryness to afford purified methyl 5-(3,4-dichlorophenylthio)pyrrole-3-carboxylate (2.76 g., m.p. 93°-96° C.).

Sources & evidence

ORD record
ord-380b642ca1a84b559c2c785a25d716a1
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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