Sodium Hydroxide → [5-(4-Chlorobenzoyl)-1-methyl-4-(methylsulfanyl)-1H-pyrrol-2-yl]acetic acid

HRID 1388929Notes

Reaction equation

HRID 1388929 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][C:5]1[N:6]([CH3:21])[C:7]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:8]([S:10][CH3:11])[CH:9]=1.[OH-].[Na+]>C(O)C>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C:12]([C:7]2[N:6]([CH3:21])[C:5]([CH2:4][C:3]([OH:22])=[O:2])=[CH:9][C:8]=2[S:10][CH3:11])=[O:20])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20469110HCID 20469110, compound

Product 1

HCID 14570947[5-(4-Chlorobenzoyl)-1-methyl-4-(methylsulfanyl)-1H-pyrrol-2-yl]acetic acidYield 82.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl-5-(p-chlorobenzoyl)-4-methylthio-1-methylpyrrole-2-acetate (19 mg) is dissolved in 0.5 ml of absolute ethanol. Aqueous sodium hydroxide (1 ml of 2.5 N solution) is added dropwise at a rate such that the reaction stayed homogeneous. Upon completion of the addition, the reaction is allowed to stand for about 30 minutes followed by precipitation with 1.5 ml of 2.5 N aqueous hydrochloride. The resulting precipitate is filtered, and dried in vacuo to afford 15 mg of 5-(p-chlorobenzoyl)-4-methylthio-1-methylpyrrole-2-acetic acid.

Workup

  1. additionUpon completion of the addition
  2. customfollowed by precipitation with 1.5 ml of 2.5 N aqueous hydrochloride
  3. filtrationThe resulting precipitate is filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9db575511d574927916c7b4483200a3b
Source dataset
uspto-grants-1984_02
Patent number
US04434175

Reaction notes

Loading…