HCID 10988627, compound → HCID 12897049, compound

HRID 1980901Notes

Reaction equation

HRID 1980901 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])[C:14]([Cl:18])=[CH:13][C:12]=1[S:19]Cl>>[Cl:10][C:11]1[CH:16]=[C:15]([Cl:17])[C:14]([Cl:18])=[CH:13][C:12]=1[S:19][C:5]1[NH:1][CH:2]=[C:3]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=1

Participants

3

Reactant 2

HCID 10988627HCID 10988627, compoundHCID 12361759methyl 1H-pyrrole-3-carboxylate

Product 1

HCID 12897049HCID 12897049, compoundYield 32.7%

Procedure

By the procedure of Example 23, methyl pyrrole-3-carboxylate (2.5 g., 20 mmoles) was reacted with 2,4,5-trichlorobenzenesulfenyl chloride (4.95 g., 20 mmoles) to yield crude product (6.0 g.) as a foam. The crude was chromatographed on 300 g. of silica gel with 200 ml. fractions of the ethyl acetate-1/hexane-7 eluant collected. Fractions 6 to 12 were combined and evaporated to yield methyl 5-(2,4,5-trichlorophenylthio)pyrrole-3-carboxylate (2.2 g., m.p. 165°-175° C.).

Workup

  1. customto yield crude product (6.0 g.) as a foam
  2. customThe crude was chromatographed on 300 g
  3. customfractions of the ethyl acetate-1/hexane-7 eluant collected
  4. customevaporated

Sources & evidence

ORD record
ord-96c3e2f1f0f74144aa4f9b61fdf7795b
Source dataset
uspto-grants-1985_04
Patent number
US04511575

Reaction notes

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