Ammonia → 4-methyl-5-phenyl-3H-[1,3]oxazine-2,6-dione

HRID 601146

Reaction equation

HRID 601146 reaction equation
[C:1]1([CH:7]([C:13]([CH3:15])=O)[C:8]([O:10][CH2:11]C)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NC(OCC)=[O:18].P(Cl)(Cl)(Cl)=O.[NH3:27]>>[CH3:15][C:13]1[NH:27][C:11](=[O:18])[O:10][C:8](=[O:9])[C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 5641Carbamic acid, ethyl esterHCID 24813Phosphorus oxychlorideHCID 95389Ethyl acetylphenylacetate

Product 1

HCID 135470884-methyl-5-phenyl-3H-[1,3]oxazine-2,6-dione

Procedure

Ethyl 2-phenylacetoacetate (1.0 g, 4.85 mmol) and urethane (0.43 g, 4.85 mmol) were heated, neat, with Phosphorous oxychloride (3 mL) at 90° C. for 3 hours. The excess reagents were removed under vacuum and the resulting residue was triturated with benzene and filtered. This solid was triturated with diethyl ether, filtered, and dried to yield 0.818 g (83%). MS (DCI/NH3) m/z 204 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 1.98 (s, 3 H) 7.28 (m, 2 H) 7.39 (m, 3 H) 11.65 (s, 1 H).

Workup

  1. customThe excess reagents were removed under vacuum
  2. customthe resulting residue was triturated with benzene
  3. filtrationfiltered
  4. customThis solid was triturated with diethyl ether
  5. filtrationfiltered
  6. customdried
  7. customto yield 0.818 g (83%)

Sources & evidence

ORD record
ord-bec4fd82910c4aeaa87b6b765ed1f8b3
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Linked notes

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