Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate

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Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate Basic information
Product Name:Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate
Synonyms:Methyl 3,4-dihydro-3-oxo-2H-benzo[b][1,4]thiazine-6-carboxylate;Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate;Methyl-3-Oxo-3,4-Dihydro-2H-1,;Methyl 3,4-dihydro-3-oxo-2H-1,4-benzothiazine-6-carboxylate;methyl 3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carboxylate;2-Methyl-3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate;Methyl 3-Oxo-2H-1,4-benzothiazine-6-carboxylate;3-keto-4H-1,4-benzothiazine-6-carboxylic acid methyl ester
CAS:188614-01-9
MF:C10H9NO3S
MW:223.25
EINECS:
Product Categories:Fused Ring Systems;Heterocycle intermediates;Esters;API intermediates
Mol File:188614-01-9.mol
Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate Structure
Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate Chemical Properties
Melting point 180-182°
Boiling point 435.7±45.0 °C(Predicted)
density 1.343±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
form Solid
pka12.34±0.20(Predicted)
AppearanceWhite to off-white Solid
CAS DataBase Reference188614-01-9(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
HazardClass IRRITANT
HS Code 2934999090
MSDS Information
Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate Usage And Synthesis
Synthesis
Methyl thioglycolate

2365-48-2

METHYL 3-AMINO-4-IODOBENZOATE

412947-54-7

Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate

188614-01-9

GENERAL METHOD: A suspension of methyl 3-iodo-4-aminobenzoate (1 mmol), methyl thioglycolate (1.5 eq.), cuprous(I) iodide (0.05 mmol), trans-N,N'-dimethylcyclohexane-1,2-diamine (0.1 mmol), and cesium carbonate (2 eq.) in anhydrous 1,4-dioxane (4 mL) was added to a vial. Nitrogen was passed into the suspension to degas it for 3 min under stirring. Subsequently, the vial was sealed. The reaction mixture was heated at 100 °C (oil bath temperature) for 15 hours. After completion of the reaction, it was cooled to room temperature and filtered. The filtrates were combined and concentrated using a rotary evaporator and the resulting residue was purified by silica gel column chromatography (eluent: 5% dichloromethane solution in methanol) to afford the target product, methyl 3-carbonyl-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate, as a beige solid.

References[1] Tetrahedron Letters, 2013, vol. 54, # 38, p. 5214 - 5216
Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate Preparation Products And Raw materials
Raw materialsMethyl thioglycolate-->Methyl 3-amino-4-iodobenzoate-->Copper(l) iodide-->(1R,2R)-N,N'-Dimethyl-1,2-cyclohexanediamine-->1,4-Dioxane-->Cesium carbonate
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