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

HRID 615211

Reaction equation

HRID 615211 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-benzoxazine-4-one are refluxed for 30 hours, whilst stirring, in 400 ml of acetonitrile with 100 g of potassium carbonate and 32 ml of chloroacetone. After the addition of a further 3.2 ml of chloroacetone, the reaction mixture is heated for a further 15 to 20 hours. The still warm reaction mixture is filtered, the residue 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 having a melting point of 125°-126°.

Workup

  1. temperaturethe reaction mixture is heated for a further 15 to 20 hours
  2. customThe still warm reaction mixture
  3. filtrationis filtered
  4. washthe residue thoroughly washed with acetone
  5. concentrationthe combined filtrate is concentrated by evaporation
  6. customThe crystalline residue is recrystallised from toluene

Sources & evidence

ORD record
ord-8758166e29b543068223044226109595
Source dataset
uspto-grants-1985_02
Patent number
US04497813

Linked notes

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