Methanol → 2-(2,4-Dichlorophenylthio)pyrrole-3-carboxylic Acid
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[NH:14][CH:13]=[C:12](C(OC)=O)[CH:11]=1.[OH-:19].[Na+].[CH3:21][OH:22]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[NH:14][CH:13]=[CH:12][C:11]=1[C:21]([OH:22])=[O:19]Participants
Procedure
Methyl 5-(2,4-dichlorophenylthio)pyrrole-3-carboxylate (3.6 g.) was combined with 40 ml. of methanol and 40 ml. of 1N sodium hydroxide and refluxed for 2.5 hours. The methanol was allowed to evaporate, the aqueous residue diluted with approximately one volume of water and extracted with ether. The aqueous phase was acidified with conc. hydrochloric acid and the heavy oil which precipitated extracted into ethyl acetate. The ethyl acetate extracts were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to crude product (3.4 g., m.p. 160°-164° C.). Recrystallization from methanol/water gave purified 5-(2,4-dichlorophenylthio)pyrrole-3-carboxylic acid (2.3 g., m.p. 166°-168° C.).
Workup
- customto evaporate
- additionthe aqueous residue diluted with approximately one volume of water
- extractionextracted with ether
- customthe heavy oil which precipitated
- extractionextracted into ethyl acetate
- washwashed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- customevaporated in vacuo to crude product (3.4 g., m.p. 160°-164° C.)
- customRecrystallization from methanol/water
- customgave
- custompurified 5-(2,4-dichlorophenylthio)pyrrole-3-carboxylic acid (2.3 g., m.p. 166°-168° C.)
Sources & evidence
- ORD record
- ord-033c2510da244a6aa31a7231032210d2
- Source dataset
- uspto-grants-1985_04
- Patent number
- US04511575
Reaction notes
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