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

HRID 548577Notes

Reaction equation

HRID 548577 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH:4]=[C:2]1[CH3:3].C(Cl)(Cl)Cl.C[Si]([N:17]=[N+]=[N-])(C)C>C(O)C>[CH3:3][C:2]1[NH:17][C:1](=[O:8])[O:7][C:5](=[O:6])[CH:4]=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, to a mixture of 44.8 g of citraconic anhydride and 60 ml of chloroform was added 50.0 g of trimethylsilylazide. The mixture was stirred at 50 to 60° C. for 5 hours. After the reaction mixture was cooled with an ice, 25.0 g of ethanol was added, followed by further stirring for 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 further stirring for 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-bb18547e7d864a3585e75cb5faf03b9a
Source dataset
uspto-grants-2011_05
Patent number
US07943614B2

Reaction notes

Loading…