Dimethylformamide → 2H-3,1-Benzoxazine-2,4(1H)-dione, 1,6-dimethyl-

HRID 542815Notes

Reaction equation

HRID 542815 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[O:8][C:7](=[O:12])[C:6]=2[CH:13]=1.[C:14](=O)([O-])[O-].[K+].[K+].CN(C)C=O.CI>O>[CH3:14][N:10]1[C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:13][C:6]=2[C:7](=[O:12])[O:8][C:9]1=[O:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide3×HCID 11430Potassium Carbonate2×HCID 2944785-Methylisatoic anhydride

Product 1

HCID 123694572H-3,1-Benzoxazine-2,4(1H)-dione, 1,6-dimethyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-methyl-1H-3,1-benzoxazine-2,4-dione (2 g), anhydrous potassium carbonate (0.64 g), dimethylformamide (10 ml) and methyl iodide (0.9 ml) was stirred at room temperature for 24 hours. More methyl iodide (0.9 ml) was added and stirring continued for a further 18 hours. More potassium carbonate (1 g) and methyl iodide (0.8 ml) were added and stirring continued for a further 23 hours. The mixture was poured on to a mixture of ice and water. The resulting precipitate was washed with water and dried to give the novel compound 1,6-dimethyl-1H-3,1-benzoxazine-2,4-dione, m.p. 165°-170°.

Workup

  1. stirringstirring
  2. waitcontinued for a further 18 hours
  3. stirringstirring
  4. waitcontinued for a further 23 hours
  5. washThe resulting precipitate was washed with water
  6. customdried

Sources & evidence

ORD record
ord-0d964eca54c94f50bbde4459bd9b3066
Source dataset
uspto-grants-1987_04
Patent number
US04659718

Reaction notes

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