1,4-Dioxane → 1-(Carbomethoxymethylcarbamoyl)-4-hydroxy-2-pyridone

HRID 466127Notes

Reaction equation

HRID 466127 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.[C:9]([CH2:12][N:13]=[C:14]=[O:15])([OH:11])=[O:10].O1CCOC[CH2:17]1>>[C:9]([CH2:12][NH:13][C:14]([N:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][C:4]1=[O:8])=[O:15])([O:11][CH3:17])=[O:10]

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 218864162-Isocyanatoacetic acidHCID 546960044-Hydroxy-2(1H)-pyridinone

Product 1

HCID 547236631-(Carbomethoxymethylcarbamoyl)-4-hydroxy-2-pyridoneYield 54%

Procedure

To 50 ml of a suspension of 2.00 g of 4-hydroxy-2-pyridone in dioxane was added 2.49 g of carboxymethylisocyanate and the resultant mixture was refluxed at 80° C. for 2 hours. After completion of the reaction, the dioxane was distilled off and diethylether was added to the residue to produce 2.20 g of the title compound in the form of solid in a yield of 54%.

Workup

  1. customAfter completion of the reaction
  2. distillationthe dioxane was distilled off
  3. additiondiethylether was added to the residue

Sources & evidence

ORD record
ord-b1c77d8040b44604aa03546a4c4bc048
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

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