Triethyl phosphite → 8-acetyl-7,8-dihydro-6,6-dimethyl-6H-[1,2,5]oxadiazolo[3,4-g][1,4]benzoxazine

HRID 1197775Notes

Reaction equation

HRID 1197775 reaction equation
[C:1]([N:4]1[C:9]2=[CH:10][C:11]3[C:12](=[N+:14]([O-])[O:15][N:16]=3)[CH:13]=[C:8]2[O:7][C:6]([CH3:19])([CH3:18])[CH2:5]1)(=[O:3])[CH3:2].P(OCC)(OCC)OCC>C1(C)C=CC=CC=1>[C:1]([N:4]1[C:9]2=[CH:10][C:11]3[C:12](=[N:14][O:15][N:16]=3)[CH:13]=[C:8]2[O:7][C:6]([CH3:19])([CH3:18])[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 191048148-acetyl-7,8-dihydro-6,6-dimethyl-6H-[1,2,5]oxadiazolo[3,4-g][1,4]benzoxazine 3-oxide

Product 1

HCID 191048118-acetyl-7,8-dihydro-6,6-dimethyl-6H-[1,2,5]oxadiazolo[3,4-g][1,4]benzoxazineYield 68.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 211 mg 8-acetyl-7,8-dihydro-6,6-dimethyl-6H-[1,2,5]oxadiazolo[3,4-g][1,4]benzoxazine 3-oxide, 15 ml toluene and 0.18 ml triethyl phosphite was heated under reflux for 16 hours, the solvent was distilled off from the reaction mixture, diethyl ether was added to the residue, and the precipitate was collected by filtration and recrystallized from 2 ml ethanol, giving 136 mg of 8-acetyl-7,8-dihydro-6,6-dimethyl-6H-[1,2,5]oxadiazolo[3,4-g][1,4]benzoxazine.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. distillationthe solvent was distilled off from the reaction mixture, diethyl ether
  4. additionwas added to the residue
  5. filtrationthe precipitate was collected by filtration
  6. customrecrystallized from 2 ml ethanol

Sources & evidence

ORD record
ord-e72e8de5602a486bb5627533b543bfd5
Source dataset
uspto-grants-1994_01
Patent number
US05278158

Reaction notes

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