Ethyl benzoylacetate → 2-amino-6-phenyl-4H-1,3-oxazin-4-one

HRID 483224Notes

Reaction equation

HRID 483224 reaction equation
C[NH:2][C:3](=[NH:5])S.OS(O)(=O)=O.[OH-].[K+].[C:13]([CH2:21][C:22]([O:24]CC)=O)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O>[NH2:5][C:3]1[O:20][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:21][C:22](=[O:24])[N:2]=1

Participants

5

Reactant 3

HCID 7170Ethyl benzoylacetateHCID 14797Potassium HydroxideHCID 178485225HCID 178485225, compound

Product 1

HCID 133709342-amino-6-phenyl-4H-1,3-oxazin-4-oneYield 76.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 9.45 g (0.034M) of methylthiopseudourea H2SO4 is added 40.0 ml of H2O+8.0 g (0.142M) of KOH. With vigorous stirring, 12.0 g (0.0625M) of ethyl benzoylacetate (Aldrich) is also added and the heterogenous mixture allowed to stir at ambient temperature for 18 hours. The resulting solids are filtered and washed very well with H2O followed by ether. The solids are dried at 60° C. in a vacuum oven to yield 7.20 g (61.3 percent) of 2-amino-6-phenyl-1,3-oxazine-4-one. An analytical sample is recrystallized from 95 percent EtOH:DMF to yield 2-amino-6-phenyl-1,3-oxazine-4-one (m.p. 244-246 d).

Workup

  1. filtrationThe resulting solids are filtered
  2. washwashed very well with H2O
  3. customThe solids are dried at 60° C. in a vacuum oven

Sources & evidence

ORD record
ord-00c3066bcb3c40ef889b3a4e43f42999
Source dataset
uspto-grants-1986_03
Patent number
US04578466

Reaction notes

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