2-Aminophenol → 2-(4-chlorophenyl)-3-oxo 3,4-dihyro-2H-1,4-benzoxazine

HRID 1439868

反応式

HRID 1439868 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])O.[Na+].Br[CH:15]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:16](Cl)=[O:17]>C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([CH:15]2[C:16](=[O:17])[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[O:8]2)=[CH:20][CH:21]=1

参加物

7

反応物 3

HCID 58012-AminophenolHCID 516892Sodium BicarbonateHCID 12575778Bromo-4-chlorophenylacetyl chloride

生成物 1

HCID 108488972-(4-chlorophenyl)-3-oxo 3,4-dihyro-2H-1,4-benzoxazine収率 76.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-aminophenol (13.5 g) in ethyl acetate (150 ml) is added a solution of sodium hydrogen carbonate (15 g) in water (300 ml), and to the mixture is added dropwise a solution of α-bromo-4-chlorophenylacetyl chloride (32.2 g) in toluene with vigorous stirring under ice cooling. After the mixture is stirred at room temperature for one hour, the solvent in the organic layer is distilled off and the residue is dissolved in acetone. To the solution is added potassium carbonate (20 g), and the mixture is stirred at room temperature overnight. The solvent is distilled off and to the residue is added water. The mixture is extracted with ethyl acetate. The ethyl acetate layer is washed, dried and distilled to remove the solvent, and the residue is recrystallized from ethyl acetate-n-hexane to give 2-(4-chlorophenyl)-3-oxo-3,4-dihyro-2H-1,4-benzoxazine (24.0 g) as crystals. M.p. 180.5°-181.5° C.

後処理

  1. stirringAfter the mixture is stirred at room temperature for one hour
  2. distillationthe solvent in the organic layer is distilled off
  3. dissolutionthe residue is dissolved in acetone
  4. additionTo the solution is added potassium carbonate (20 g)
  5. stirringthe mixture is stirred at room temperature overnight
  6. distillationThe solvent is distilled off and to the residue
  7. additionis added water
  8. extractionThe mixture is extracted with ethyl acetate
  9. washThe ethyl acetate layer is washed
  10. customdried
  11. distillationdistilled
  12. customto remove the solvent
  13. customthe residue is recrystallized from ethyl acetate-n-hexane

出典と根拠

ORDレコード
ord-4fb08c1d204a4bee84804cf7c61d8d01
出典データセット
uspto-grants-1996_03
特許番号
US05496815

関連ノート

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