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

HRID 519046노트

반응식

HRID 519046 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 19096565Water ethanol용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-659afda124bc49f7937e84d476672ccf
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115151B2

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