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

HRID 1618641노트

반응식

HRID 1618641 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3c9c705aa7c74808b7bb55e0f8e63cf3
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765940B2

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