Hydrogen Peroxide → HCID 86743401, compound

HRID 1608204Notes

Reaction equation

HRID 1608204 reaction equation
[NH2:1][C:2]1[C:25]([Cl:26])=[CH:24][C:5]([C:6]([NH:8][CH2:9][CH:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[CH2:11]2)=[O:7])=[C:4]([O:27][CH2:28][CH3:29])[CH:3]=1.[OH:30]O>CO>[NH2:1][C:2]1[C:25]([Cl:26])=[CH:24][C:5]([C:6]([NH+:8]([O-:30])[CH2:9][CH:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[CH2:11]2)=[O:7])=[C:4]([O:27][CH2:28][CH3:29])[CH:3]=1

Participants

4

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 3087020HCID 3087020, compound

Product 1

HCID 86743401HCID 86743401, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-amino-5-chloro-N-[[4-(2-chlorobenzyl)-2-morpholinyl]methyl]-2-ethoxybenzamide (4.0 g) in methanol (150 ml) is added 30% aqueous hydrogen peroxide (1.2 g). After the mixture is heated under reflux for 8 hours, an additional 30% aqueous hydrogen peroxide (1.2 g) is added, and the reaction mixture is refluxed with stirring for an additional 24 hours. The solvent is distilled off under reduced pressure, and chloroform and water are added to the residue. The mixture is stirred for about 30 minutes. The precipitate is collected and recrystallized from isopropyl alcohol-diisopropyl ether to give the title compound (0.6 g), mp 154°-157° C.

Workup

  1. temperatureAfter the mixture is heated
  2. temperatureunder reflux for 8 hours
  3. temperaturethe reaction mixture is refluxed
  4. distillationThe solvent is distilled off under reduced pressure, and chloroform and water
  5. additionare added to the residue
  6. stirringThe mixture is stirred for about 30 minutes
  7. customThe precipitate is collected
  8. customrecrystallized from isopropyl alcohol-diisopropyl ether

Sources & evidence

ORD record
ord-5e33e65526984a58a21a4772a757e915
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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