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

HRID 348983

反応式

HRID 348983 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5ebcb16739f74f90aa96197bb81c0e20
出典データセット
uspto-grants-2007_02
特許番号
US07176242B2

関連ノート

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