Ammonium Chloride → 7-Amino-4-methyl-4h-benzo[1,4]thiazin-3-one

HRID 896153Notes

Reaction equation

HRID 896153 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][C:10]([N+:12]([O-])=O)=[CH:11][C:6]=2[S:5][CH2:4][C:3]1=[O:15].[Cl-].[NH4+]>CCO.O.[Fe]>[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][C:10]([NH2:12])=[CH:11][C:6]=2[S:5][CH2:4][C:3]1=[O:15]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 218777807-Nitro-4-methyl-4H-benzo[1,4]thiazin-3-one

Product 1

HCID 218777707-Amino-4-methyl-4h-benzo[1,4]thiazin-3-oneYield 93%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 3,4-dihydro-4-methyl-7-nitro-2H-1,4-benzothiazin-3-one (4.50 g, 20.07 mmol) in EtOH (100 mL) and water (50 mL) is added ammonium chloride (10.76 g, 200.7 mmol). To this mixture is added iron (3.37 g, 60.21 mmol) in 3 equal portions. The resulting mixture is heated to 80° C. for 2 h at which time the reaction is cooled to room temperature. This mixture is filtered and the filtrate is concentrated under reduced pressure and extracted with EtOAc (3×50 mL). The organic phase is washed with water and saline, dried over MgSO4, and concentrated under reduced pressure to give the title compound (for reference see DE 19802239) as a dark brown oil (3.60 g, 93%), MS m/z 195.5 (M+H)+.

Workup

  1. temperatureis cooled to room temperature
  2. filtrationThis mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. extractionextracted with EtOAc (3×50 mL)
  5. washThe organic phase is washed with water and saline
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7723d591242a4294baa85d23ac875280
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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