Sodium Hydroxide → 6-Nitro-2H-benzo[b][1,4]thiazin-3(4H)-one

HRID 519046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 519046
Cl[C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].[SH:12][CH2:13][C:14](OC)=[O:15].[OH-].[Na+]>CCO.O>[N+:9]([C:6]1[CH:7]=[CH:8][C:2]2[S:12][CH2:13][C:14](=[O:15])[NH:4][C:3]=2[CH:5]=1)([O-:11])=[O:10]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 16907Methyl ThioglycolateHCID 226912-Chloro-5-nitroaniline

Produkt 1

HCID 41823566-Nitro-2H-benzo[b][1,4]thiazin-3(4H)-oneAusbeute 11,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-5-nitroaniline (15 g, 87 mmol), methyl 2-mercaptoacetate (13.8 g, 130 mmol) and sodium hydroxide (10.4 g, 261 mmol) in EtOH/water (250 mL, v/v=10:1) was heated at reflux for 16 h. The reaction mixture was cooled to ambient temperature, the solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (eluting with 17% EtOAc in petroleum ether) to give 6-nitro-2H-benzo[b][1,4]thiazin-3(4H)-one (2.1 g, 11%). LC/MS (Table 1, Method 2) Rt=0.790 min; MS m/z: 211 [M+H]+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. customthe solvent was removed in vacuo
  4. customthe residue was purified by column chromatography on silica gel (eluting with 17% EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-659afda124bc49f7937e84d476672ccf
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115151B2

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