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

HRID 519046ノート

反応式

HRID 519046 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 19096565Water ethanol溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-659afda124bc49f7937e84d476672ccf
出典データセット
uspto-grants-2015_08
特許番号
US09115151B2

反応ノート

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