tert-Butyl hydroperoxide → 5-(5-Bromo-2-fluorophenyl)-5,6-dihydro-5-methyl-2H-1,4-oxazin-3-amine

HRID 925446Notes

Reaction equation

HRID 925446 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([C:8]2([CH3:15])[NH:13][C:12](=S)[CH2:11][O:10][CH2:9]2)[CH:7]=1.C(OO)(C)(C)C.[NH4+:23].[OH-]>N.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([C:8]2([CH3:15])[CH2:9][O:10][CH2:11][C:12]([NH2:23])=[N:13]2)[CH:7]=1

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 14923Ammonium HydroxideHCID 888502225-(5-Bromo-2-fluorophenyl)-5-methylmorpholine-3-thione

Product 1

HCID 669315715-(5-Bromo-2-fluorophenyl)-5,6-dihydro-5-methyl-2H-1,4-oxazin-3-amine

Reagents, catalysts & solvents 1

HCID 21705897Ammonia methanolSolvent

Procedure

To a suspension of 5-(5-bromo-2-fluoro-phenyl)-5-methyl-morpholine-3-thione (14.0 g, 46 mmol) in 7N NH3/MeOH (308 ml) was added tBuOOH (72.8 ml of a 70% aq. soln.) and NH4OH (131.6 ml of a 25% aq. soln.). The reaction mixture was stirred over night at rt, quenched with aq. Na2S2O3 soln., concentrated and extracted with EtOAc to give the title compound that was used in the next step without further purification.

Workup

  1. customquenched with aq. Na2S2O3 soln
  2. concentration, concentrated
  3. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-76271570a62e4b4395778e76518f8a25
Source dataset
uspto-grants-2016_03
Patent number
US09284284B2

Reaction notes

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