Isopropyl Acetate → 1,4-Dihydro-2H-3,1-benzoxazin-2-one

HRID 1155332

Reaction equation

HRID 1155332 reaction equation
[C:1]([C:4]1C=C[CH:9]=[CH:8][C:5]=1CO)(=O)[NH2:2].Cl[O-].[Na+].[C:15]([O:18][CH:19]([CH3:21])C)(=[O:17])C>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].[Br-].[Na+]>[O:17]=[C:15]1[NH:2][C:1]2[CH:4]=[CH:5][CH:8]=[CH:9][C:21]=2[CH2:19][O:18]1

Participants

6

Reactant 3

HCID 7915Isopropyl AcetateHCID 99176o-(Hydroxymethyl)benzamideHCID 23665760Sodium Hypochlorite

Product 1

HCID 257861,4-Dihydro-2H-3,1-benzoxazin-2-oneYield 70%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 253881Sodium BromideCatalyst

Conditions

Temperature
50 °C

Procedure

143 g (0.948 moles) of 2-carbamoyl-benzyl alcohol, 2.3 g (0.0226 moles) of sodium bromide, 6.7 g of Adogen 464 and 806 ml of isopropyl acetate were stirred together in a two liter flask and cooled in a water bath. 504 ml of a 14% w/v solution of sodium hypochlorite (1.0 mole) was added to the stirred mixture over 40 minutes and at 30° C. Vigorous agitation was maintained during the addition and for a further 2 hours. The two-phase reaction mixture was then warmed to 50° C. to dissolve all solids. The organic phase was separated and the medium distilled off. The formed solid was recrystallized from 3 volumes of toluene to form 99 g of the desired product as a pale brown solid; m.p. 112° C.; yield 70%.

Workup

  1. temperaturecooled in a water bath
  2. temperatureVigorous agitation was maintained during the addition and for a further 2 hours
  3. customThe two-phase reaction mixture
  4. dissolutionto dissolve all solids
  5. customThe organic phase was separated
  6. distillationthe medium distilled off
  7. customThe formed solid was recrystallized from 3 volumes of toluene

Sources & evidence

ORD record
ord-0311b1672fa44c47bcae52f2aaf5b5d3
Source dataset
uspto-grants-1981_11
Patent number
US04301283

Linked notes

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