Azobisisobutyronitrile → N-(3-chlorophenyl)-2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide

HRID 377556Notes

Reaction equation

HRID 377556 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:27])[C:10]([N:13]2[C:18](=[O:19])[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:16]([CH3:26])[O:15][CH2:14]2)([CH3:12])[CH3:11])[CH:5]=[CH:6][CH:7]=1.[Br:28]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:27])[C:10]([N:13]2[C:18](=[O:19])[C:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[C:16]([CH2:26][Br:28])[O:15][CH2:14]2)([CH3:12])[CH3:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimide2×HCID 19354647N-(3-chlorophenyl)-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide

Product 1

HCID 19354652N-(3-chlorophenyl)-2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamideYield 8.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of N-(3-chlorophenyl)-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (1.0 g), N-bromosuccinimide (0.45 g), azobis-isobutyronitrile (10 mg) in carbon tetrachloride was heated at 65° C. for 2 hours. A second addition of N-bromosuccinimide (0.1 g) was made and the solution heated at 65° C. for a further 2 hours. The solution was then allowed to cool and the solvent removed under reduced pressure to give a brown residue, which was purified by dry column chromatography on silica, eluting with ethyl acetate/dichloromethane to give N-(3-chlorophenyl)-2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (compound 8, 0.1 g) as a white solid, m.p. 89.8-90.8° C.

Workup

  1. temperaturethe solution heated at 65° C. for a further 2 hours
  2. temperatureto cool
  3. customthe solvent removed under reduced pressure
  4. customto give a brown residue, which
  5. customwas purified
  6. customby dry column chromatography on silica
  7. washeluting with ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-8134bc6fefa24ddf8e64885203c102b3
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

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