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

HRID 74061

반응식

HRID 74061 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 5963Benzyltrimethylammonium chloride촉매HCID 6212Chloroform용매

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-40ba61ee9c604417a896c4992bf6d27b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829204B2

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