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

HRID 1618641Notes

Reaction equation

HRID 1618641 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3c9c705aa7c74808b7bb55e0f8e63cf3
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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