Sodium Carbonate → 2-(1,1-Dioxo-1lambda6-[1,2]thiazinan-2-yl)-N-hydroxy-N-methyl-benzamidine

HRID 1822719Notes

Reaction equation

[O:1]=[S:2]1(=[O:16])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]#[N:11].Cl.[CH3:18][NH:19][OH:20].C(=O)([O-])[O-].[Na+].[Na+]>O.C(O)C>[O:1]=[S:2]1(=[O:16])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]([N:19]([OH:20])[CH3:18])=[NH:11]

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred solution of 2-(1,1-dioxo-1λ6-[1,2]thiazinan-2-yl)-benzonitrile and N-methylhydroxylamine hydrochloride (1.67 g, 20 mmol) in 1:1 water/ethanol (70 mL) was added sodium carbonate (1.06 g, 10 mmol) and the resulting mixture stirred at 90° C. for 18 h. After cooling and concentration, the resulting residue was suspended in MeOH/CHCl3 (100 mL, 1:9). The insoluble solids were removed by filtration and concentration of the filtrate gave the crude product as an amber oil (3.5 g) that was carried on without further purification. LCMS calcd for C12H17N3O3S (M+H): 284.35; found: 284.27.

Workup

temperatureAfter cooling
concentrationconcentration
customThe insoluble solids were removed by filtration and concentration of the filtrate

Sources & evidence

ORD record: ord-547ad588dfdb42c7919465fecb97d662
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07037908B2

Reaction notes

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