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

HRID 5845

반응식

HRID 5845 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])O.[Na+].Br[C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH2:22][C:23](Cl)=[O:24]>C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[Cl:21][C:19]1[CH:20]=[CH:15][C:16]([CH:22]2[C:23](=[O:24])[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[O:8]2)=[CH:17][CH:18]=1

참가 물질

7

반응물 3

HCID 58012-AminophenolHCID 516892Sodium BicarbonateHCID 197942342-Bromo-p-chlorophenylacetyl chloride

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

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 o-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.

후처리

  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

출처 및 근거

ORD 기록
ord-ffca69bda88f4569b98eca5bd5ca7c45
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246929

연결된 노트

불러오는 중…