Sodium Hydroxide → 5-(3-Chlorophenylthio)pyrrole-3-carboxylic acid

HRID 894021Notes

Reaction equation

HRID 894021 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[NH:13][CH:12]=[C:11]([C:14]([O:16]C)=[O:15])[CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[NH:13][CH:12]=[C:11]([C:14]([OH:16])=[O:15])[CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12897032Methyl 5-(3-Chlorophenylthio)pyrrole-3-carboxylate

Product 1

HCID 128970335-(3-Chlorophenylthio)pyrrole-3-carboxylic acidYield 92.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl 5-(3-chlorophenylthio)pyrrole-3-carboxylate (1.5 g.) was refluxed with 10 ml. of 1 N sodium hydroxide and 20 ml. of methanol, at which time thin layer chromatography (silica gel with hexane-5/ethyl acetate-1/5% acetic acid as eluant) indicated hydrolysis was complete. The methanol was allowed to evaporate. The aqueous residue was diluted with approximately one volume of water and extracted twice with ether. The aqueous phase was acidified with 6 N hydrochloric acid and product extracted multiply into ethyl acetate. The combined ethyl acetate extracts were back-washed with water and then with saturated brine, dried over anhydrous sodium sulfate and evaporated to an oil. Trituration of the oil with hexane gave 5-(3-chlorophenylthio)pyrrole-3-carboxylic acid (1.32 g., m.p. 134°-137° C., m/e 253).

Workup

  1. customhydrolysis
  2. customto evaporate
  3. additionThe aqueous residue was diluted with approximately one volume of water
  4. extractionextracted twice with ether
  5. extractionextracted multiply into ethyl acetate
  6. washThe combined ethyl acetate extracts were back-washed with water
  7. dry with materialwith saturated brine, dried over anhydrous sodium sulfate
  8. customevaporated to an oil

Sources & evidence

ORD record
ord-4345c3ac9dc942a5b519def5e7e233b5
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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