Isatoic Anhydride → Benz-3,1-oxazine-2,4-dione, 1-pentyl-

HRID 910172Notes

Reaction equation

HRID 910172 reaction equation
[NH:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[O:3][C:2]1=[O:12].[H-].[Na+].I[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(OCC)(=O)C>CN(C)C=O>[CH2:16]([N:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[O:3][C:2]1=[O:12])[CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 8359Isatoic AnhydrideHCID 8857Ethyl AcetateHCID 123351-IodopentaneHCID 24758Sodium hydride

Product 1

HCID 143462Benz-3,1-oxazine-2,4-dione, 1-pentyl-Yield 44.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,1-Benzoxazin-2,4-(1H)-dione (1.0 g, 6.13 mmol) was dissolved in N,N-dimethylformamide (10 ml), 60% sodium hydride (0.296 g, 7.39 mmol) was added under ice-cooling, and the mixture was stirred at room temperature for 1 hr. 1-Iodopentane (0.97 ml, 7.32 mmol) was added, and the mixture was stirred at room temperature for 2 hr. Ethyl acetate was added to the reaction mixture, the mixture was washed with water, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give 1-pentyl-3,1-benzoxazin-2,4-(1H)-dione (0.634 g, 2.72 mmol, yield 44%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 2 hr
  3. washthe mixture was washed with water
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-b9e499a4478c455aaa55cb8eae592382
Source dataset
uspto-grants-2011_09
Patent number
US08022072B2

Reaction notes

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