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

HRID 4523

反応式

HRID 4523 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

70 g of 2,3-dihydro-2,2-dimethyl-6-hydroxy-4H-1,3-benzoxazin-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°.

後処理

  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

出典と根拠

ORDレコード
ord-469f9aa04d4a4ee282aa8435ec72848a
出典データセット
uspto-grants-1988_02
特許番号
US04727067

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