Hydrogen Peroxide → 6-[4-(4-Bromo-3-methyl-phenylsulfinyl)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one

HRID 463071Notes

Reaction equation

HRID 463071 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]3[NH:22][C:21](=[O:23])[O:20][C:19]([CH3:25])([CH3:24])[C:18]=3[CH:26]=2)=[CH:4][C:3]=1[CH3:27].[OH:28]O.O>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]3[NH:22][C:21](=[O:23])[O:20][C:19]([CH3:24])([CH3:25])[C:18]=3[CH:26]=2)=[O:28])=[CH:4][C:3]=1[CH3:27]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 13260528HCID 13260528, compound

Product 1

HCID 132605556-[4-(4-Bromo-3-methyl-phenylsulfinyl)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

An amount of 9.2 gm (0.02 mol) of 6-[4-(4-bromo-3-methyl-phenylmercapto)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one is dissolved in 100 ml of glacial acetic acid, and 2 ml (0.02 mol) of 30% hydrogen peroxide are added. The mixture is stirred for three hours at ambient temperature, poured onto 400 ml of water, and extracted three times with ethyl acetate. The organic phase is washed with water and dried with sodium sulfate, and the ethyl acetate is distilled off. The solid residue is recrystallized from ethyl acetate/diisopropyl ether.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried with sodium sulfate
  4. distillationthe ethyl acetate is distilled off
  5. customThe solid residue is recrystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-25408b17c3674ca1ac72e8410f1ed15b
Source dataset
uspto-grants-1985_05
Patent number
US04518597

Reaction notes

Loading…