Hydrochloric Acid → 5-(4-Chlorophenylthio)pyrrole-3-carboxylic Acid

HRID 1980893Notes

Reaction equation

HRID 1980893 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[NH:13][CH:12]=[C:11]([C:14]([O:16]C)=[O:15])[CH:10]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[NH:13][CH:12]=[C:11]([C:14]([OH:16])=[O:15])[CH:10]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12897034Methyl 5-(4-chlorophenylthio)pyrrole-3-carboxylate

Product 1

HCID 128970355-(4-Chlorophenylthio)pyrrole-3-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-(4-chlorophenylthio)pyrrole-3-carboxylate (1.4 g.) was combined with 20 ml. of methanol and 20 ml. of 1N sodium hydroxide and heated on a steam bath for 2 hours. The reaction was cooled, acidified with conc. hydrochloric acid. and the crude product which precipitated, collected by filtration. Two recrystallizations from acetone/hexane afforded purified 5-(4-chlorophenylthio)pyrrole-3-carboxylic acid (740 mg., m.p. 171°-173° C.).

Workup

  1. temperatureThe reaction was cooled
  2. customand the crude product which precipitated
  3. filtrationcollected by filtration
  4. customTwo recrystallizations from acetone/hexane
  5. customafforded
  6. custompurified 5-(4-chlorophenylthio)pyrrole-3-carboxylic acid (740 mg., m.p. 171°-173° C.)

Sources & evidence

ORD record
ord-25ce3ccaa16f41a9b70e18d3aba29f89
Source dataset
uspto-grants-1985_04
Patent number
US04511575

Reaction notes

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