Hydrogen Peroxide → N-(4-tert-butyl-3-hydroxy-phenyl)-1-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-2-carboxamide

HRID 383443Notes

Reaction equation

HRID 383443 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([CH:14]2[CH2:19][NH:18][C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[S:15]2)=[O:13])=[CH:7][C:6]=1[OH:24])([CH3:4])([CH3:3])[CH3:2].[OH:25]O>C(O)(=O)C.CN(C=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([CH:14]2[S:15](=[O:25])[C:16]3[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=3[NH:18][CH2:19]2)=[O:13])=[CH:7][C:6]=1[OH:24])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 59395005N-(4-tert-butyl-3-hydroxy-phenyl)-3,4-dihydro-2H-1,4-benzothiazine-2-carboxamide

Product 1

HCID 59394956N-(4-tert-butyl-3-hydroxy-phenyl)-1-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-2-carboxamideYield 38.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-(4-tert-butyl-3-hydroxy-phenyl)-3,4-dihydro-2H-1,4-benzothiazine-2-carboxamide (20 mg, 0.058 mmol) in acetic acid (500 μL) was treated with hydrogen peroxide (12 μL of aq. 30% w/w, 0.12 mmol) and stirred at room temperature for 2 h. The reaction was diluted with DMF and purified by HPLC (10-99% CH3CN/5 mM HCl) to provide N-(4-tert-butyl-3-hydroxy-phenyl)-1-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-2-carboxamide (8 mg, 38% yield). LC/MS m/z 359.2 [M+H]+.

Workup

  1. custompurified by HPLC (10-99% CH3CN/5 mM HCl)

Sources & evidence

ORD record
ord-cee83edfb0d14c63ba59d36970f85851
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

Loading…