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

HRID 519046Notes

Reaction equation

HRID 519046 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

HCID 41823566-Nitro-2H-benzo[b][1,4]thiazin-3(4H)-oneYield 11.5%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-659afda124bc49f7937e84d476672ccf
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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