Sodium Hydroxide → HCID 12897027, compound

HRID 894015Notes

Reaction equation

HRID 894015 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 1 N 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 6 N 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-carboxlic 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-carboxlic acid (590 mg., m.p. 151°-153° C., m/e 233)

Sources & evidence

ORD record
ord-bb121f5ecdee48d587c2de5aff8b5ee3
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

Loading…