3-Oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carbaldehyde synthesis

3synthesis methods

Product Name:3-Oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carbaldehyde
CAS Number:262426-58-4
Molecular formula:C9H7NO2S
Molecular Weight:193.22

443955-31-5 Synthesis

6-(HydroxyMethyl)-2h-benzo[b][1,4]thiazin-3(4h)-one

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3-Oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carbaldehyde

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Yield:262426-58-4 56%

Reaction Conditions:

with manganese(IV) oxide in tetrahydrofuran;chloroform at 70; for 4 h;

Steps:

H.C 3-Oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carbaldehyde

C. To a solution of 6-hydroxymethyl-4H-benzo[1,4]thiazin-3-one (360 mg, 1.8 mmol) in THF/CHCl₃ (2:1, 18 mL) was added MnO₂ (1.6 g, 18 mmol) and the resulting suspension was heated to 70° C. and stirred for 4 h. The suspension was filtered through diatomaceous earth and the filtrate was concentrated. The resulting solid was triturated with EtOAc/hexanes (1:1) and a minimal amount of CH₃OH to provide 200 mg (56%) of the title compound as a tan solid. MS (ESI): exact mass calculated for C₉H₇NO₂S, 193.02; m/z found, 194.1 [M+H]⁺. ¹H NMR (500 MHz, CDCl₃): 9.94 (s, 1H), 8.78 (brs, 1H), 7.54-7.49 (m, 2H), 7.37 (d, J=1.5, 1H), 3.52 (s, 2H).

References:

US2006/223810,2006,A1 Location in patent:Page/Page column 22

Acetic acid, [(4-formyl-2-nitrophenyl)thio]-, methyl ester

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References

709-58-0 Synthesis

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References