Chloroacetone → 2,3-dihydro-2,2-dimethyl-6-(2-oxopropoxy)-4H-1,3-benzoxazin-4-one

HRID 980281Notes

Reaction equation

HRID 980281 reaction equation
[CH3:1][C:2]1([CH3:14])[NH:7][C:6](=[O:8])[C:5]2[CH:9]=[C:10]([OH:13])[CH:11]=[CH:12][C:4]=2[O:3]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:22][C:23](=[O:25])[CH3:24]>C(#N)C>[CH3:1][C:2]1([CH3:14])[NH:7][C:6](=[O:8])[C:5]2[CH:9]=[C:10]([O:13][CH2:22][C:23](=[O:25])[CH3:24])[CH:11]=[CH:12][C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 6571Chloroacetone2×HCID 11430Potassium CarbonateHCID 137543316-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1,3-benzoxazin-4-one

Product 1

HCID 137543322,3-dihydro-2,2-dimethyl-6-(2-oxopropoxy)-4H-1,3-benzoxazin-4-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

70 g of 2,3-dihydro-2,2-dimethyl-6-hydroxy-4H-1,3-benzoxazin-4-one in 400 ml of acetonitrile with 100 g of potassium carbonate and 32 ml of chloroacetone are stirred under reflux for 30 hours. After the addition of a further 3.2 ml of chloroacetone, the reaction mixture is refluxed for a further 15-20 hours. The reaction mixture is filtered whilst still warm; the residue is thoroughly washed with acetone, and the combined filtrate is concentrated by evaporation. The crystalline residue is recrystallised from toluene and yields 2,3-dihydro-2,2-dimethyl-6-(2-oxopropoxy)-4H-1,3-benzoxazin-4-one, m.p. 125°-126°.

Workup

  1. temperatureunder reflux for 30 hours
  2. temperaturethe reaction mixture is refluxed for a further 15-20 hours
  3. filtrationThe reaction mixture is filtered
  4. temperaturewhilst still warm
  5. washthe residue is thoroughly washed with acetone
  6. concentrationthe combined filtrate is concentrated by evaporation
  7. customThe crystalline residue is recrystallised from toluene

Sources & evidence

ORD record
ord-be078bdc9ffa4cac9c19ff92109974fc
Source dataset
uspto-grants-1987_01
Patent number
US04636511

Reaction notes

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