Hydrogen Peroxide → HCID 12694258, compound

HRID 426709Notes

Reaction equation

HRID 426709 reaction equation
[N:1]1([C:6]([NH:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[CH:11][C:10]=2[S:19][CH3:20])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:21]O>C(O)(=O)C>[N:1]1([C:6]([NH:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[CH:11][C:10]=2[S:19]([CH3:20])=[O:21])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 12694257N-[4,5-Dimethoxy-2-(methylthio)phenyl]-1-pyrrolidinecarboxamide

Product 1

HCID 12694258HCID 12694258, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A reaction mixture containing 52 g. of N-pyrrolidinylcarbonyl-2-methylthio-4,5-dimethoxyaniline 19.8 ml. of 31 percent aqueous hydrogen peroxide and 1 l. of glacial acetic acid was stirred for about 20 hours at ambient temperature. The reaction mixture was then concentrated under reduced pressure to a residual wax. The residue was dissolved in 1 l. of methylene chloride and the methylene chloride layer washed twice with water and then dried. Removal of the methylene chloride in vacuo yielded a residue comprising N-pyrrolidinylcarbonyl-2-methylsulfinyl-4,5-dimethoxyaniline which, after recrystallization from a benzene-hexane solvent mixture, yielded material melting at 124°-7° C. (80 percent yield).

Workup

  1. additionA reaction mixture containing 52 g
  2. concentrationThe reaction mixture was then concentrated under reduced pressure to a residual wax
  3. dissolutionThe residue was dissolved in 1 l
  4. washof methylene chloride and the methylene chloride layer washed twice with water
  5. customdried
  6. customRemoval of the methylene chloride in vacuo

Sources & evidence

ORD record
ord-cb5fa1033558425ca6fdccc622542c83
Source dataset
uspto-grants-1979_10
Patent number
US04171361

Reaction notes

Loading…