Methyl iodide → 5-Chloro-3,4-dimethyl-2H-1,3-oxazine-2,6(3H)-dione

HRID 549206Notes

Reaction equation

HRID 549206 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[O:6][C:5](=[O:9])[NH:4][C:3]=1[CH3:10].[C:11](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[Cl:1][C:2]1[C:7](=[O:8])[O:6][C:5](=[O:9])[N:4]([CH3:11])[C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 122582495-chloro-4-methyl-2H-1,3-oxazine-2,6(3H)-dione

Product 1

HCID 576721385-Chloro-3,4-dimethyl-2H-1,3-oxazine-2,6(3H)-dioneYield 75.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

At room temperature, 2.11 g of 5-chloro-4-methyl-2H-1,3-oxazine-2,6(3H)-dione, 2.07 g of potassium carbonate and 1.3 ml of methyl iodide were sequentially added to 40 ml of acetone, then the mixture was stirred for 3 hours under heat refluxing condition. To the reaction mixture was added 0.5 ml of methyl iodide, and the mixture was further stirred for 2 hours under heat refluxing condition. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The resulting solid was dried to obtain 1.74 g of 5-chloro-3,4-dimethyl-2H-1,3-oxazine-2,6(3H)-dione represented by the formula:

Workup

  1. temperatureunder heat
  2. temperaturerefluxing condition
  3. stirringthe mixture was further stirred for 2 hours
  4. temperatureunder heat
  5. temperaturerefluxing condition
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe resulting solid was dried

Sources & evidence

ORD record
ord-096190ba9df04067958eed872d155757
Source dataset
uspto-grants-2011_05
Patent number
US07943638B2

Reaction notes

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