Chloroform → 4-Methyl-2H-1,3-oxazine-2,6(3H)-dione

HRID 549202Notes

Reaction equation

HRID 549202 reaction equation
C[Si]([N:5]=[N+]=[N-])(C)C.[C:8]1(=[O:15])[O:14][C:12](=[O:13])[CH:11]=[C:9]1[CH3:10].C(Cl)(Cl)Cl>C(O)C>[CH3:10][C:9]1[NH:5][C:8](=[O:15])[O:14][C:12](=[O:13])[CH:11]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 12012Citraconic AnhydridesHCID 78378Azidotrimethylsilane

Product 1

HCID 5357074-Methyl-2H-1,3-oxazine-2,6(3H)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

At room temperature, 50.0 g of trimethylsilylazide was added to a mixture of 44.8 g of citraconic anhydride and 60 ml of chloroform. The mixture was stirred at 50-60° C. for 5 hours. After cooling the reaction mixture with an ice, 25.0 g of ethanol was added, followed by stirring for additional 30 minutes. The resulting solid was collected by filtration, and washed with a mixed solvent of chloroform and ethanol to obtain crude 4-methyl-2H-1,3-oxazine-2,6(3H)-dione represented by the formula:

Workup

  1. additionwas added
  2. stirringby stirring for additional 30 minutes
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-567f8d9e56d444b4aeb1c2072ce050cf
Source dataset
uspto-grants-2011_05
Patent number
US07943638B2

Reaction notes

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