methyl 1H-pyrrole-3-carboxylate → HCID 12897036, compound

HRID 894025Notes

Reaction equation

HRID 894025 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]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[S:18]Cl>C(Cl)Cl>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[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 128785412,5-Dichlorobenzenesulfenyl chloride

Product 1

HCID 12897036HCID 12897036, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, methyl pyrrole-3-carboxylate (2.5 g., 20 mmoles) was dissolved in 50 ml. of methylene chloride and cooled with stirring in an ice-water bath. 2,5-Dichlorobenzenesulfenyl chloride (4.24 g., 20 mmoles) was added dropwise. The bath was removed and the reaction stirred for 1 hour at room temperature, at which time thin layer chromatography (silica gel with ethyl acetate-1/hexane-5/5% acetic acid as eluant) indicated that virtually all of the starting pyrrole ester had been consumed. An equal volume of ether was added, the mixture filtered and the filtrate evaporated in vacuo to a partially crystalline gum (5.2 g.). The latter was recrystallized from methylene chloride/hexane to yield purified methyl 5-(2,5-dichlorophenylthio)pyrrole-3-carboxylate (2.68 g., m.p. 162°-165° C.).

Workup

  1. customThe bath was removed
  2. stirringthe reaction stirred for 1 hour at room temperature, at which time thin layer chromatography (silica gel with ethyl acetate-1/hexane-5/5% acetic acid as eluant)
  3. customhad been consumed
  4. additionAn equal volume of ether was added
  5. filtrationthe mixture filtered
  6. customthe filtrate evaporated in vacuo to a partially crystalline gum (5.2 g.)
  7. customThe latter was recrystallized from methylene chloride/hexane
  8. customto yield
  9. custompurified methyl 5-(2,5-dichlorophenylthio)pyrrole-3-carboxylate (2.68 g., m.p. 162°-165° C.)

Sources & evidence

ORD record
ord-12400ebb711a4bad840338f332ac48f2
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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