Sodium Hydroxide → HCID 12897043, compound

HRID 1703267Notes

Reaction equation

HRID 1703267 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 1 N 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-f296564dc07d464e8316157bb88b774f
Source dataset
uspto-grants-1982_09
Patent number
US04351843

Reaction notes

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