methyl 1H-pyrrole-3-carboxylate → Methyl 5-(2,4-Dichlorophenylthio)pyrrole-3-carboxylate

HRID 894027Notes

Reaction equation

HRID 894027 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:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[S:18]Cl>C(Cl)Cl>[Cl:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[S:18][C:5]1[NH:1][CH:2]=[C:3]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=1

Participants

4

Reactant 2

HCID 12361759methyl 1H-pyrrole-3-carboxylateHCID 128785422,4-Dichlorobenzenesulfenyl chloride

Product 1

HCID 20401058Methyl 5-(2,4-Dichlorophenylthio)pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, methyl pyrrole-3-carboxylate (3.75 g.) was dissolved in 100 ml. of methylene chloride and cooled in an ice-water bath. To the cold, stirred solution, 2,4-dichlorobenzenesulfenyl chloride (6.39 g., 30 mmoles) was added dropwise. The bath was removed and the reaction stirred at room temperature for 1 hour. An equal volume of ether was added, the mixture filtered and the filtrate evaporated in vacuo to crude product (9.0 g., oil). The oil was chromatographed on 300 g. of silica gel with 200 ml. fractions of the ethyl acetate-1/hexane-7 eluant collected. Fractions 6 to 10 were combined and evaporated to yield purified methyl 5-(2,4-dichlorophenylthio)pyrrole-3-carboxylate (3.7 g., solid, m/e 302).

Workup

  1. additionwas added dropwise
  2. customThe bath was removed
  3. additionAn equal volume of ether was added
  4. filtrationthe mixture filtered
  5. customthe filtrate evaporated in vacuo to crude product (9.0 g., oil)
  6. customThe oil was chromatographed on 300 g
  7. customfractions of the ethyl acetate-1/hexane-7 eluant collected
  8. customevaporated
  9. customto yield
  10. custompurified methyl 5-(2,4-dichlorophenylthio)pyrrole-3-carboxylate (3.7 g., solid, m/e 302)

Sources & evidence

ORD record
ord-58f1a0e2627d41aaac54300932cb7d5a
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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