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

HRID 1915389Notes

Reaction equation

HRID 1915389 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-f888a2ddaebb4a7eaa3665a7b1290f04
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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