Ammonium Chloride → HCID 86727415, compound

HRID 519050Notes

Reaction equation

HRID 519050 reaction equation
[CH3:1][CH:2]1[C:7](=[O:8])[NH:6][N:5]=[C:4]2[CH2:9][S:10][C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:12]=3[N:3]12.[NH4+].[Cl-]>CO.C1COCC1.[Zn]>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]2[S:10][CH2:9][C:4]3=[N:5][NH:6][C:7](=[O:8])[CH:2]([CH3:1])[N:3]3[C:12]=2[CH:13]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86727414HCID 86727414, compound

Product 1

HCID 86727415HCID 86727415, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methyl-9-nitro-3,5-dihydrobenzo[5,6][1,4]thiazino[3,4-c][1,2,4]triazin-2(1H)-one (0.308 g, 1.11 mmol) in MeOH (25 mL) and THF (25 mL) was added powdered zinc (0.724 g, 11.1 mmol) and NH4Cl (0.592 g, 11.1 mmol) and the mixture was heated at reflux for 16 h. After cooling to ambient temperature, the mixture was filtered to give crude 9-amino-1-methyl-3,5-dihydrobenzo[5,6][1,4]thiazino[3,4-c][1,2,4]triazin-2(1H)-one (100%), which was used in the next step directly without further purification. TLC (eluting with 50% EtOAc/PE) Rf=0.3.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 h
  3. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-389d0db9225b461b92c7ee23ac09c2f0
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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