Acetone → N-(3-chlorophenyl)-2-(2,3-dihydro-6-iodomethyl-4-oxo-5-phenyl-4H-2,3-oxazin-3-yl)-2-methylpropanamide

HRID 377555Notes

Reaction equation

HRID 377555 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:28])[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]([CH2:26]Br)OC2)([CH3:12])[CH3:11])[CH:5]=[CH:6][CH:7]=1.[I-:29].[Na+].C[C:32](C)=[O:33]>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:28])[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]([CH2:26][I:29])[CH2:32][O:33]2)([CH3:11])[CH3:12])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 19354652N-(3-chlorophenyl)-2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide2×

Product 1

HCID 70253527N-(3-chlorophenyl)-2-(2,3-dihydro-6-iodomethyl-4-oxo-5-phenyl-4H-2,3-oxazin-3-yl)-2-methylpropanamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of N-(3-chlorophenyl)-2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (compound 8, 0.2 g) and sodium iodide (0.065 g) in acetone was heated under reflux for 18 hours, then evaporated to give a residue which was redissolved in ether. The ethereal solution was washed in turn with saturated aqueous sodium thiosulphate solution and water, dried (magnesium sulphate) and evaporated under reduced pressure to leave a residue which was purified by dry column chromatography on silica, eluting with ethyl acetate/dichloromethane to give N-(3-chlorophenyl)-2-(2,3-dihydro-6-iodomethyl-4-oxo-5-phenyl-4H-2,3-oxazin-3-yl)-2-methylpropanamide (compound 9, 0.04 g) as a white solid, m.p. 134.6-136.6° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customevaporated
  4. customto give a residue which
  5. washThe ethereal solution was washed in turn with saturated aqueous sodium thiosulphate solution and water
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated under reduced pressure
  8. customto leave a residue which
  9. customwas purified
  10. customby dry column chromatography on silica
  11. washeluting with ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-2d742cc0fdb5484c99a2a35976805918
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

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