Chloroacetyl chloride → Methyl 8-bromo-4-butyl-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

HRID 348983

반응식

HRID 348983 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([NH:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].C(=O)(O)[O-].[Na+].[CH3:23][C:24](CC(C)C)=O.O.ClCC(Cl)=O>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:11]2[O:12][CH2:24][CH2:23][N:13]([CH2:14][CH2:15][CH2:16][CH3:17])[C:10]=2[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=1

참가 물질

6

반응물 4

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 21086159Methyl 3-bromo-5-(butylamino)-4-hydroxybenzoateHCID 22737866Isobutyl methyl ketone water

생성물 1

HCID 21086218Methyl 8-bromo-4-butyl-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To an ice-cold, stirred solution of Methyl 3-bromo-5-(butylamino)-4-hydroxybenzoate (440 mg) and sodium bicarbonate (280 mg) in 1:1 isobutyl methyl ketone/water (10 mL) was added chloroacetyl chloride (226 mg). The mixture was stirred for 1 h, warmed to room temperature, and heated at reflux for 14 h. The mixture was cooled to room temperature, diluted with chloroform, and the layer separated. The organic layer was washed with water, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure to give a white solid: 1H NMR (300 MHz, CDCl3) δ 7.94, 7.62, 4.76, 3.98, 3.93, 1.65, 1.43, 0.97, which was used in the next step without further purification or characterization.

후처리

  1. temperatureheated
  2. temperatureat reflux for 14 h
  3. temperatureThe mixture was cooled to room temperature
  4. customthe layer separated
  5. washThe organic layer was washed with water, and brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give a white solid
  10. custom1H NMR (300 MHz, CDCl3) δ 7.94, 7.62, 4.76, 3.98, 3.93, 1.65, 1.43, 0.97, which was used in the next step without further purification or characterization

출처 및 근거

ORD 기록
ord-5ebcb16739f74f90aa96197bb81c0e20
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

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