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

HRID 74061

反応式

HRID 74061 の反応式
Cl[CH2:2][C:3](Cl)=[O:4].[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([NH2:16])[CH:10]=1)([O-:8])=[O:7].C([O-])(O)=O.[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.C(Cl)(Cl)Cl>[N+:6]([C:9]1[CH:14]=[CH:13][C:12]2[O:15][CH2:2][C:3](=[O:4])[NH:16][C:11]=2[CH:10]=1)([O-:8])=[O:7]

参加物

6

反応物 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 36133892-Amino-4-Nitrophenol

生成物 1

HCID 27636836-Nitro-2H-1,4-benzoxazin-3(4H)-one収率 41.2%

試薬・触媒・溶媒 2

HCID 5963Benzyltrimethylammonium chloride触媒HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

At 0° C., chloroacetyl chloride (8.75 mL, 0.11 mol) was added dropwise to a mixture of 4-nitro-2-aminophenol (15.4 g, 0.1 mol), benzyltrimethylammonium chloride (18.6 g, 0.1 mol) and NaHCO3 (42 g, 0.5 mol) in chloroform (350 ml) over a period of 30 min. After addition, the reaction mixture was stirred at 0° C. for 1 h, then at 50° C. overnight. The solvent was removed under reduced pressure and the residue was treated with water (50 ml). The solid was collected via filtration, washed with water and recrystallized from ethanol to provide 6-nitro-4H-benzo[1,4]oxazin-3-one as a pale yellow solid (8 g, 41%).

後処理

  1. additionAfter addition
  2. customat 50° C.
  3. customovernight
  4. customThe solvent was removed under reduced pressure
  5. additionthe residue was treated with water (50 ml)
  6. filtrationThe solid was collected via filtration
  7. washwashed with water
  8. customrecrystallized from ethanol

出典と根拠

ORDレコード
ord-40ba61ee9c604417a896c4992bf6d27b
出典データセット
uspto-grants-2014_09
特許番号
US08829204B2

関連ノート

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