Hydrogen Peroxide → 2-amino-N-(2-methoxyphenyl)-6-(4-nitrophenyl)sulfinyl-benzamide

HRID 1476707

Reaction equation

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

Participants

Conditions

Temperature: 66 °C

Procedure

Compound 25 (1.0 equiv.) was dissolved in CH3OH (30 mL) with a magnetic stirrer at RT, and 35% H2O2 (3.0 equiv.) was added slowly to this solution. This reaction mixture was heated in an oil bath at 66° C. and monitored using TLC. The reaction was quenched with MnO2 at RT. The mixture was filtered and the residue was washed with ethyl acetate (3×5 mL). The liquid layer was concentrated under reduced pressure and the oily residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether) to provide a yellow solid; 44.3% yield;

Workup

customThe reaction was quenched with MnO2 at RT
filtrationThe mixture was filtered
washthe residue was washed with ethyl acetate (3×5 mL)
concentrationThe liquid layer was concentrated under reduced pressure
customthe oily residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether)
customto provide a yellow solid

Sources & evidence

ORD record: ord-68ff612d1b96417d9b4870621bb3ef95
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09402819B2

Linked notes

Loading…