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

HRID 443860Notes

Reaction equation

HRID 443860 reaction equation
[CH3:1][C:2]1[CH:13]=[C:6]2[C:7]([O:9][C:10](=[O:12])[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8].[C:14](=O)([O-])[O-].[Na+].[Na+].IC>CN(C)C=O>[CH3:14][N:11]1[C:10](=[O:12])[O:9][C:7](=[O:8])[C:6]2=[CH:13][C:2]([CH3:1])=[CH:3][CH:4]=[C:5]12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 2944785-Methylisatoic anhydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 26.6 g of 5-methylisatoic anhydride in 150 ml of dimethylformamide is treated with 17.5 g of anhydrous sodium carbonate, then with 32 g of iodomethane, and the mixture is stirred at 20°-25° C. for 18 hrs. The reaction mixture is poured into 1.25 liter of ice water and the resulting precipitate of N,5-dimethylisatoic anhydride is collected by filtration, washed with water and dried; mp 166°-169° C.

Workup

  1. filtrationthe resulting precipitate of N,5-dimethylisatoic anhydride is collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-5a9a9fd139584d019663cb13f6e44f20
Source dataset
uspto-grants-1981_04
Patent number
US04261997

Reaction notes

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