Water → 2H-3,1-Benzoxazine-2,4(1H)-dione, 6-chloro-1-methyl-

HRID 635512Notes

Reaction equation

HRID 635512 reaction equation
[Cl: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.O>CN(C)C=O>[Cl:1][C:2]1[CH:13]=[C:6]2[C:7]([O:9][C:10](=[O:12])[N:11]([CH3:14])[C:5]2=[CH:4][CH:3]=1)=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 784805-Chloroisatoic anhydride

Product 1

HCID 267242H-3,1-Benzoxazine-2,4(1H)-dione, 6-chloro-1-methyl-Yield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4.95 g (25.1 mmol) of 5-chloroisatoic anhydride in 80 mL of dry N,N-dimethylformamide (DMF) was added 5.15 g (48.6 mmol) of powdered sodium carbonate forming a suspension. The suspension was then treated with 2.00 mL (4.86 g; 32.1 mmol) of iodomethane. The resulting suspension was stirred for 13 hours, then it was poured into 300 mL of water with vigorous stirring. After 2-3 minutes the resulting precipitate was filtered, and washed with 200 mL of water. The filter cake was dissolved in 200 mL of dichloromethane and this solution was dried (Na2SO4). The solution was concentrated in vacuo and the residue triturated with ethyl acetate-hexane (1:3). The solid was filtered, washed with ethyl acetate-hexane (1:3), and finally hexane. The solid was dried in vacuo to give 3.90 g (73%) of the title compound as a pale yellow solid. 1H NMR (300 MHz, DMSO-D6) d 3.42 (s, 3 H), 7.44 (d, 1 H), 7.85 (d, 1 H0, 7.83, (d, 1 H), 7.92 (d, 1 H). MS (Cl Mode) m/z 212 (M+H, 100%), 240 (M+29, 8%). HPLC analysis showed a single peak.

Workup

  1. filtrationAfter 2-3 minutes the resulting precipitate was filtered
  2. washwashed with 200 mL of water
  3. dissolutionThe filter cake was dissolved in 200 mL of dichloromethane
  4. dry with materialthis solution was dried (Na2SO4)
  5. concentrationThe solution was concentrated in vacuo
  6. customthe residue triturated with ethyl acetate-hexane (1:3)
  7. filtrationThe solid was filtered
  8. washwashed with ethyl acetate-hexane (1:3), and finally hexane
  9. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-1eb1da5ba2494e4b8b851b7d84ef802f
Source dataset
uspto-grants-2001_02
Patent number
US06187923B1

Reaction notes

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