Dimethylformamide → HCID 4352988, compound

HRID 1175791Notes

Reaction equation

HRID 1175791 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+].CN(C)C=O.[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>O>[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:1]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[C:4](=[O:11])[O:3][C:2]2=[O:12])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8359Isatoic AnhydrideHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 4352988HCID 4352988, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2H-3,1-benzoxazine-2,4(1H)-dione (18.7 g), sodium hydride (an oily, about 66%, 4.8 g) and N,N-dimethylformamide (70 ml) was added dropwise 4-methoxybenzyl chloride (17.6 ml), stirred at room temperature for 1 night. To the reaction mixture was added water and extracted with ethyl acetate. The extract was washed with water and a saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to obtain the target compound (26.1 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materiala saturated brine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8ff2bf4358fe44f59d1c66113e61ef9a
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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