Sodium Hydroxide → HCID 12897040, compound

HRID 894032Notes

Reaction equation

HRID 894032 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[S:10][C:11]1[NH:15][CH:14]=[C:13]([C:16]([O:18]C)=[O:17])[CH:12]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[S:10][C:11]1[NH:15][CH:14]=[C:13]([C:16]([OH:18])=[O:17])[CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 12897049HCID 12897049, compound

Product 1

HCID 12897040HCID 12897040, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl 5-(2,4,5-trichlorophenylthio)pyrrole-3-carboxylate (2.1 g.) was combined with 20 ml. of methanol and 20 ml. of 1 N sodium hydroxide and heated to reflux. Additional 1 N sodium hydroxide was added in an amount sufficient to obtain a solution. Reflux was continued for 2.5 hours, the methanol was then allowed to evaporate, and the aqueous residue was diluted with approximately one volume of water and extracted twice with ether. The aqueous phase was cooled in an ice-water bath and acidified with conc. hydrochloric acid. Crude product (1.65 g., m.p. 210°-215° C.) was recovered by filtration. Recrystallization from methanol/water afforded purified 5-(2,4,5-trichlorophenylthio)pyrrole-3-carboxylic acid (1.01 g., m.p. 215°-217° C.).

Workup

  1. customto obtain a solution
  2. temperatureReflux
  3. customto evaporate
  4. additionthe aqueous residue was diluted with approximately one volume of water
  5. extractionextracted twice with ether
  6. temperatureThe aqueous phase was cooled in an ice-water bath
  7. filtrationCrude product (1.65 g., m.p. 210°-215° C.) was recovered by filtration
  8. customRecrystallization from methanol/water
  9. customafforded
  10. custompurified 5-(2,4,5-trichlorophenylthio)pyrrole-3-carboxylic acid (1.01 g., m.p. 215°-217° C.)

Sources & evidence

ORD record
ord-057d09ffa20147978b6d48a1b600415a
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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