Hydroxylamine → HCID 11391154, compound

HRID 851918Notes

Reaction equation

HRID 851918 reaction equation
CC1(C)[O:6][CH:5]([CH:7]2[C:12](=[O:13])[NH:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[S:8]2)[C:4](=O)[O:3]1.[NH2:20][OH:21]>C1COCC1>[OH:6][CH:5]([CH:7]1[C:12](=[O:13])[NH:11][C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[S:8]1)[C:4]([NH:20][OH:21])=[O:3]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 69002385HCID 69002385, compound

Product 1

HCID 11391154HCID 11391154, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

The crude 2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-4H-benzo[1,4]thiazin-3-one (0.036 mmol) is dissolved in 0.5 mL of THF and 0.5 mL of NH2OH (1N in MeOH) is added to the mixture. After the addition, the mixture is stirred at 60° C. for 3 hours. The solvent is then removed under vacuum and the residue is purified by preparative thin layer chromatography (silica gel, 10% MeOH/CH2Cl2) to provide the title compound 2,N-dihydroxy-2-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-yl)-acetamide. Yield: 70%. 1H NMR (400 MHz, MeOD) δ 7.30 (dd, 1H, J=1.29 Hz, J=8.0 Hz), 7.18, (dt, 1H, J=1.3 Hz, J=8.0 Hz), 7.01 (dt, 1H, J=1.3 Hz, J=8.0 Hz), 6.95 (dd, 1H, J=1.3 Hz, J=8.0 Hz), 4.74 (d, 1H, J=3.80), 3.97 (d, 1H, J=3.8). MS: (ES+): 255.1[M+1].

Workup

  1. additionAfter the addition
  2. customThe solvent is then removed under vacuum
  3. customthe residue is purified by preparative thin layer chromatography (silica gel, 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-d9f6439ba2d744ea9914bc4025557874
Source dataset
uspto-grants-2007_08
Patent number
US07253164B2

Reaction notes

Loading…