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

HRID 1618641Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1618641
[OH-].[Na+].[SH:3][CH2:4][C:5]([O:7]CC)=O.Cl[C:11]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:12]=1[NH2:13]>CCO.CCOC(C)=O>[N+:18]([C:15]1[CH:16]=[CH:17][C:11]2[S:3][CH2:4][C:5](=[O:7])[NH:13][C:12]=2[CH:14]=1)([O-:20])=[O:19]

Komponenten

6

Edukt 3

HCID 12185Ethyl ThioglycolateHCID 14798Sodium HydroxideHCID 226912-Chloro-5-nitroaniline

Produkt 1

HCID 41823566-Nitro-2H-benzo[b][1,4]thiazin-3(4H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2.44M aqueous NaOH (24 mL, 58 mmol) was added to a stirring solution of ethyl 2-mercaptoacetate (19 mL, 174 mmol) in EtOH (150 mL). The mixture was added to the stirring solution of 2-chloro-5-nitroaniline (10 g, 58 mmol) in EtOH (68 ml). The resulting mixture was heated at reflux overnight. After this time the reaction was diluted with EtOAc and washed with water. The separated organic layer was dried over Mg2SO4, filtered and evaporated in vacuo. The crude residue was triturated with EtOAc to give 6-nitro-2H-benzo[b]-[1,4]thiazin-3(4H)-one. Mass Spectrum (ESI) m/e=257 (M+1).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. washwashed with water
  4. dry with materialThe separated organic layer was dried over Mg2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude residue was triturated with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-3c9c705aa7c74808b7bb55e0f8e63cf3
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765940B2

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