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

HRID 970562Notes

Reaction equation

HRID 970562 reaction equation
[CH3:1][C:2]1[CH:13]=[CH:12][C:5]2[NH:6][C:7](=[O:11])[O:8][C:9](=[O:10])[C:4]=2[CH:3]=1.[H-].[Na+].[CH3:16]I>CN(C=O)C>[CH3:16][N:6]1[C:5]2[CH:12]=[CH:13][C:2]([CH3:1])=[CH:3][C:4]=2[C:9](=[O:10])[O:8][C:7]1=[O:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2944785-Methylisatoic anhydride

Product 1

HCID 123694572H-3,1-Benzoxazine-2,4(1H)-dione, 1,6-dimethyl-Yield 91.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of Compound 11 (5 g, 28 mmol) in DMF was added slowly to a suspension of NaH (60% in mineral oil, 1.24 g, 31 mmol) in DMF and further stirred at room temperature for 1 h. Then, methyl iodide (1.92 mL, 31 mmol) was added and further stirred at room temperature for 3 h. The solution was poured into ice water and the solids formed were filtered, washed several times by water, and dried. The solids were suspended in hexane, sonicated briefly, filtered, and washed by hexane to yield 4.9 g (74%) of white solids. M.P. 153° C. 1H NMR (DMSO-d6): δ 2.32 (s, 3H), 3.52 (s, 3H), 7.38 (d, J=8.6 Hz, 1H), 7.54 (dd, J=1.7, 8.2 Hz, 1H), 7.83 (d, J=1.2 Hz, 1H).

Workup

  1. stirringfurther stirred at room temperature for 3 h
  2. customthe solids formed
  3. filtrationwere filtered
  4. washwashed several times by water
  5. customdried
  6. customsonicated briefly
  7. filtrationfiltered
  8. washwashed by hexane

Sources & evidence

ORD record
ord-949a4eaeb64f4b48a80192d60679679a
Source dataset
uspto-grants-2007_12
Patent number
US07312221B2

Reaction notes

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