Chloroacetyl chloride → 6-Bromo-2H-1,4-benzoxazin-3(4H)-one

HRID 519197

反応式

HRID 519197 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[OH:9].C([O-])(O)=O.[Na+].Cl[CH2:16][C:17](Cl)=[O:18]>CC(C)CC(=O)C.O>[Br:8][C:6]1[CH:5]=[CH:4][C:3]2[O:9][CH2:16][C:17](=[O:18])[NH:1][C:2]=2[CH:7]=1

参加物

6

反応物 3

HCID 6577Chloroacetyl chlorideHCID 3518402-Amino-4-BromophenolHCID 516892Sodium Bicarbonate

生成物 1

HCID 162181426-Bromo-2H-1,4-benzoxazin-3(4H)-one収率 89%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 7909Methyl Isobutyl Ketone溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-amino-4-bromophenol (25 g, 133.0 mmol), NaHCO3 (22.4 g, 266.0 mmol) in 4-methylpentan-2-one (50 mL) and water (50 mL) at 0° C. was added 2-chloroacetyl chloride (10.0 mL, 200.0 mmol) dropwise. The reaction mixture was stirred at 80° C. for 24 h then cooled to ambient temperature and filtered. The filtrate was washed with water (3×10 mL) and dried over anhydrous Na2SO4. After filtration, the organic phase was evaporated to give 6-bromo-4H-benzo[1,4]oxazin-3-one as a white solid (27 g, 89%). 1H NMR (CDCl3, 400 MHz): δ 8.49 (brs, 1H), 7.08 (dd, J=8.4 Hz, J=2.0 Hz, 1H), 6.93 (d, J=2.0 Hz, 1H), 6.87 (d, J=8.4 Hz, 1H), 4.61 (s, 2H).

後処理

  1. temperaturethen cooled to ambient temperature
  2. filtrationfiltered
  3. washThe filtrate was washed with water (3×10 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationAfter filtration
  6. customthe organic phase was evaporated

出典と根拠

ORDレコード
ord-d9310ec8cee44c6c80903629941d1172
出典データセット
uspto-grants-2015_08
特許番号
US09115151B2

関連ノート

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