Sodium Hydroxide → HCID 12897043, compound

HRID 1980906Notes

Reaction equation

HRID 1980906 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([S:9][C:10]2[NH:14][CH:13]=[C:12]([C:15]([O:17]C)=[O:16])[CH:11]=2)[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+]>CO>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[C:5]([S:9][C:10]2[NH:14][CH:13]=[C:12]([C:15]([OH:17])=[O:16])[CH:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13064266HCID 13064266, compound

Product 1

HCID 12897043HCID 12897043, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl 5-(3-trifluoromethylphenylthio)pyrrole-3-carboxylate (2.9 g.) was combined with 30 ml. of methanol and 30 ml. of 1N sodium hydroxide and refluxed for 2.5 hours. The methanol was allowed to evaporate and the aqueous residue washed twice with ether. The aqueous phase was acidified with conc. hydrochloric acid and the crude product (2.3 g) which precipitated, was recovered by filtration. Recrystallization of the crude from methanol/water gave purified 5-(3-trifluoromethylphenylthio)pyrrole-3-carboxylic acid (1.47 g., m.p. 138°-140° C.).

Workup

  1. customto evaporate
  2. washthe aqueous residue washed twice with ether
  3. customthe crude product (2.3 g) which precipitated
  4. filtrationwas recovered by filtration
  5. customRecrystallization of the crude from methanol/water
  6. customgave
  7. custompurified 5-(3-trifluoromethylphenylthio)pyrrole-3-carboxylic acid (1.47 g., m.p. 138°-140° C.)

Sources & evidence

ORD record
ord-ff8cf8029e1544cd89e2494b23959a2e
Source dataset
uspto-grants-1985_04
Patent number
US04511575

Reaction notes

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