Methane → 1-(3,5-difluorophenyl)-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-propan-1-one

HRID 1274880Notes

Reaction equation

HRID 1274880 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([OH: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]=[C:6]([F:8])[CH:7]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC.C>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([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]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 3283Diethyl EtherHCID 221183241-(3,5-difluorophenyl)-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 221182601-(3,5-difluorophenyl)-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-propan-1-oneYield 61.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(3,5-difluorophenyl)-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropan-1-ol (0.96 g) in dichloromethane was added to a stirred mixture of pyridinium chlorochromate (0.83 g) and powdered molecular sieve (4A) in dichloromethane at 20° C. After 18 hours, ether and charcoal were added, the mixture filtered through hyflo and evaporated to give 1-(3,5-difluorophenyl)-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropan-1-one (0.59 g) as a beige solid, m.p. 156.8-157.8° C.

Workup

  1. filtrationthe mixture filtered through hyflo
  2. customevaporated

Sources & evidence

ORD record
ord-85e16c3d24844e7d8645669d25da9418
Source dataset
uspto-grants-2000_12
Patent number
US06159902

Reaction notes

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