Sodium Hydroxide → 5-(3,4-Dichlorophenylthio)pyrrole-3-carboxylic Acid

HRID 1703261Notes

Reaction equation

HRID 1703261 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[NH:14][CH:13]=[C:12]([C:15]([O:17]C)=[O:16])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[NH:14][CH:13]=[C:12]([C:15]([OH:17])=[O:16])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12897048Methyl 5-(3,4-Dichlorophenylthio)pyrrole-3-carboxylate

Product 1

HCID 128970395-(3,4-Dichlorophenylthio)pyrrole-3-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl 5-(3,4-dichlorophenylthio)pyrrole-3-carboxylate (1.7 g.) was combined with 20 ml. of methanol and 20 ml. of 1 N sodium hydroxide and refluxed for 3 hours. The methanol was allowed to evaporate, and approximately one volume of water was added to the aqueous residue, which was then extracted twice with ether, cooled in an ice-water bath, acidified with conc. hydrochloric acid, and the product extracted into ethyl acetate. The three ethyl acetate extracts were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a gummy solid which was crystallized by trituration with hexane and recovered by filtration (1.34 g., m.p. 156°-159° C.). Recrystallization from chloroform gave purified 5-(3,4-dichlorophenylthio)pyrrole-3-carboxylic acid (850 mg., m.p. 159°-161° C.).

Workup

  1. customto evaporate
  2. additionapproximately one volume of water was added to the aqueous residue, which
  3. extractionwas then extracted twice with ether
  4. temperaturecooled in an ice-water bath
  5. extractionthe product extracted into ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo to a gummy solid which
  10. customwas crystallized by trituration with hexane
  11. filtrationrecovered by filtration (1.34 g., m.p. 156°-159° C.)
  12. customRecrystallization from chloroform
  13. customgave
  14. custompurified 5-(3,4-dichlorophenylthio)pyrrole-3-carboxylic acid (850 mg., m.p. 159°-161° C.)

Sources & evidence

ORD record
ord-b5dfc97098eb4d3bb28d3eae327c7e81
Source dataset
uspto-grants-1982_09
Patent number
US04351843

Reaction notes

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