Water → HCID 21411824, compound

HRID 2071696Notes

Reaction equation

HRID 2071696 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:19][C:20]#N)[N:5]([CH3:18])[C:6]=1[C:7](=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:16])=[O:15])=[CH:10][CH:9]=1.[OH-:22].[Na+].[OH2:24]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:19][C:20]([OH:24])=[O:22])[N:5]([CH3:18])[C:6]=1[C:7](=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:16])=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21411892HCID 21411892, compound

Product 1

HCID 21411824HCID 21411824, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 0.50 g of 4-chloro-1-methyl-5-(p-methylsulfinylbenzoyl)-pyrrole-2-acetonitrile from Example XLV is stirred and refluxed in a solution of 0.13 g sodium hydroxide in 2 ml H2O and 2 ml 95% ethanol for 2 hours. The whole is then poured into water and the resulting aqueous solution is washed with chloroform. The washed aqueous solution is then acidified to pH 1 with 3N HCl. The solid which precipitates is collected by filtration and is recrystallized from 10:1 chloroform: water to give 4-chloro-1-methyl-5-(p-methylsulfinylbenzoyl)-pyrrole-2-acetic acid as a yellow solid; m.p. 222°-223° C.

Workup

  1. washthe resulting aqueous solution is washed with chloroform
  2. customThe solid which precipitates
  3. filtrationis collected by filtration
  4. customis recrystallized from 10:1 chloroform

Sources & evidence

ORD record
ord-8490e8ddf2aa40a69cd6a11c8b4ee459
Source dataset
uspto-grants-1977_09
Patent number
US04048191

Reaction notes

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