Hydroxylamine → HCID 11391154, compound

HRID 2105533Notes

Reaction equation

HRID 2105533 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-fb79e383032b4b478b188689b4a0aee2
Source dataset
uspto-grants-2009_08
Patent number
US07579363B2

Reaction notes

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