Sodium Hydroxide → HCID 12897038, compound

HRID 894026Notes

Reaction equation

HRID 894026 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]=[C:6]([Cl:8])[CH:7]=1.[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]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20400955HCID 20400955, compound

Product 1

HCID 12897038HCID 12897038, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl 5-(3,5-dichlorophenylthio)pyrrole-3-carboxylate (2.5 g.) was combined with 25 ml. of methanol and 25 ml. of 1 N sodium hydroxide and refluxed for 3 hours. The methanol was allowed to evaporate, the aqueous residue diluted with approximately one volume of water and washed twice with ether. The aqueous phase was acidified with conc. hydrochloric acid and the product extracted into ethyl acetate. The two ethyl acetate extracts were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to crude product (1.84 g., m.p. 169°-172° C.). Recrystallization from chloroform afforded purified 5-(3,5-dichlorophenylthio)-pyrrole-3-carboxylic acid (1.3 g., m.p. 175°-177° C.).

Workup

  1. customto evaporate
  2. additionthe aqueous residue diluted with approximately one volume of water
  3. washwashed twice with ether
  4. extractionthe product extracted into ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo to crude product (1.84 g., m.p. 169°-172° C.)
  9. customRecrystallization from chloroform
  10. customafforded
  11. custompurified 5-(3,5-dichlorophenylthio)-pyrrole-3-carboxylic acid (1.3 g., m.p. 175°-177° C.)

Sources & evidence

ORD record
ord-15804d9f8d1d44f3a1385a1d054f2ff9
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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