Dichloromethane → Methyl 5-(4-chlorophenylthio)pyrrole-3-carboxylate

HRID 894022Notes

Reaction equation

HRID 894022 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[CH:2]1.C(Cl)Cl.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]Cl)=[CH:16][CH:15]=1>CCOCC>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][C:5]2[NH:1][CH:2]=[C:3]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 110844654-ChlorobenzenesulfenylchlorideHCID 12361759methyl 1H-pyrrole-3-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-c7efac28c35c49dab8597778cfc95f96
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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