Sodium Hydroxide → HCID 12897027, compound

HRID 1980885Notes

Reaction equation

HRID 1980885 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[NH:13][CH:12]=[C:11]([C:14]([O:16]C)=[O:15])[CH:10]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[NH:13][CH:12]=[C:11]([C:14]([OH:16])=[O:15])[CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12897026HCID 12897026, compound

Product 1

HCID 12897027HCID 12897027, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-(2-methylphenylthio)pyrrole-3-carboxylate (1.1 g.) was combined with 20 ml. of 1N sodium hydroxide and 50 ml. of methanol and refluxed for 2.5 hours, at which time thin layer chromatography with hexane-5/ethyl acetate-1/5% acetic acid as eluant indicated reaction to be complete. Methanol was removed by evaporation, the aqueous residue was diluted with approximately one volume of water, and extracted with ether. The aqueous phase was acidified with 6N hydrochloric acid and the product extracted into ethyl acetate. The ethyl acetate was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to crude product (1.0 g.). Recrystallization from methylene chloride/hexane gave purified 5-(2-methylphenylthio)pyrrole-3-carboxylic acid (590 mg., m.p. 151°-153° C., m/e 233).

Workup

  1. customreaction
  2. customMethanol was removed by evaporation
  3. additionthe aqueous residue was diluted with approximately one volume of water
  4. extractionextracted with ether
  5. extractionthe product extracted into ethyl acetate
  6. washThe ethyl acetate was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo to crude product (1.0 g.)
  10. customRecrystallization from methylene chloride/hexane
  11. customgave
  12. custompurified 5-(2-methylphenylthio)pyrrole-3-carboxylic acid (590 mg., m.p. 151°-153° C., m/e 233)

Sources & evidence

ORD record
ord-123fa9c8b109400cb9575c32d79e226f
Source dataset
uspto-grants-1985_04
Patent number
US04511575

Reaction notes

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