Hydrazine hydrate (1:1) → HCID 86727414, compound

HRID 519049Notes

Reaction equation

HRID 519049 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]2[S:8][CH2:9][C:10](=S)[N:11]([CH:12]([CH3:18])[C:13](OCC)=[O:14])[C:6]=2[CH:5]=1)([O-:3])=[O:2].O.[NH2:23][NH2:24]>CCO>[CH3:18][CH:12]1[C:13](=[O:14])[NH:24][N:23]=[C:10]2[CH2:9][S:8][C:7]3[CH:20]=[CH:21][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=3[N:11]12

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86727413HCID 86727413, compound

Product 1

HCID 86727414HCID 86727414, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(6-nitro-3-thioxo-2H-benzo[b][1,4]thiazin-4(3H)-yl)propanoate (0.475 g, 1.455 mmol) in EtOH (30 mL) was added hydrazine hydrate (0.364 g, 7.28 mmol) and the mixture was then heated at reflux for 16 h. After cooling to ambient temperature gradually, the precipitate was collected by filtration to give 1-methyl-9-nitro-3,5-dihydrobenzo[5,6][1,4]thiazino[3,4-c][1,2,4]-triazin-2(1H)-one (0.312 g, 77%), which was used in the next step directly without further purification. TLC (eluting with 33% EtOAc in petroleum ether) Rf=0.3.

Workup

  1. temperaturethe mixture was then heated
  2. temperatureat reflux for 16 h
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-6a9b2500c8f44b97ad6f9c22413271ce
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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