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

HRID 1197776Notes

Reaction equation

HRID 1197776 reaction equation
C([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]([CH3:18])([CH3:17])[CH2:5]1)(=O)C.CO.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:17][C:6]1([CH3:18])[CH2:5][NH:4][C:9]2=[CH:10][C:11]3[C:12](=[N:14][O:15][N:16]=3)[CH:13]=[C:8]2[O:7]1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 191048118-acetyl-7,8-dihydro-6,6-dimethyl-6H-[1,2,5]oxadiazolo[3,4-g][1,4]benzoxazine

Product 1

HCID 1356750137,8-dihydro-6,6-dimethyl-6H-[1,2,5]oxadiazolo[3,4-g][1,4]benzoxazineYield 100.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.22 g 8-acetyl-7,8dihydro-6,6-dimethyl-6H-[1,2,5]oxadiazolo[3,4-g][1,4]benzoxazine, 40 ml methanol, 4 ml water and 1.37 g potassium carbonate was stirred at room temperature for one hour, the reaction mixture was poured into 300 ml ice water, and the resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, the solvents were distilled off from the dried solution, and the residue was subjected to column chromatography on silica gel. Elution was conducted by the use of a 2:1 mixture of hexane and ethyl acetate, giving 1.02 g of 7,8-dihydro-6,6-dimethyl-6H-[1,2,5]oxadiazolo[3,4-g][1,4]benzoxazine.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. distillationthe solvents were distilled off from the dried solution
  4. washElution
  5. additionwas conducted by the use of a 2:1 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-9995002fb0894b4696d1734d2eed6319
Source dataset
uspto-grants-1994_01
Patent number
US05278158

Reaction notes

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