Aniline → N-phenyl-2-methyl-2-(6-methyl-5-phenyl-2 3-dihydro-4-oxo-4H-1,3-oxazin-3-yl)-propanamide

HRID 1600534Notes

Reaction equation

HRID 1600534 reaction equation
[CH3:1][C:2]([N:7]1[C:12](=[O:13])[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:10]([CH3:20])[O:9][CH2:8]1)([CH3:6])[C:3]([OH:5])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(N(CC)CC)C>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[C:41]1([NH:40][C:3](=[O:5])[C:2]([CH3:1])([N:7]2[C:12](=[O:13])[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:10]([CH3:20])[O:9][CH2:8]2)[CH3:6])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 22118282HCID 22118282, compound

Product 1

HCID 21829889N-phenyl-2-methyl-2-(6-methyl-5-phenyl-2 3-dihydro-4-oxo-4H-1,3-oxazin-3-yl)-propanamideYield 55.1%

Reagents, catalysts & solvents 1

HCID 22996148Carbon tetrachloride methylene chlorideSolvent

Procedure

To a suspension of 2-methyl-2-(6-methyl-5-phenyl-2,3-dihydro-4-oxo-4H-1,3-oxazin-3-yl)-propionic acid (0.83 g) in 10.4 ml of CCl4 --CH2Cl2 (1:1) was added triphenylphosphin (1.04 g), then the mixture was refluxed for 40 min. The reaction mixture was ice-cooled and aniline (0.28 g) and triethylamine (0.3 g) were slowly added, then it was stirred at room temperature for 1 h. After evaporation of the solvent, the residue was dissolved in ethyl acetate. The insolubles were filtered off and the filtrate was evaporated. The residue was purified by chromatography on a silica gel column to get the captioned compound (0.58 g).

Workup

  1. temperaturethe mixture was refluxed for 40 min
  2. temperaturecooled
  3. customAfter evaporation of the solvent
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. filtrationThe insolubles were filtered off
  6. customthe filtrate was evaporated
  7. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-b620cbd457d64dee8bd73ac6f4c4cc3d
Source dataset
uspto-grants-1999_11
Patent number
US05977025

Reaction notes

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