Methyl 2-isocyanatoacetate → 1-(Carbomethoxymethylcarbamoyl)-4-hydroxy-2-pyridone

HRID 1607322Notes

Reaction equation

HRID 1607322 reaction equation
[C:1]([CH2:5][N:6]=[C:7]=[O:8])([O:3][CH3:4])=[O:2].[OH:9][C:10]1[CH:15]=[CH:14][NH:13][C:12](=[O:16])[CH:11]=1>O1CCOCC1>[C:1]([CH2:5][NH:6][C:7]([N:13]1[CH:14]=[CH:15][C:10]([OH:9])=[CH:11][C:12]1=[O:16])=[O:8])([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 2769479Methyl 2-isocyanatoacetateHCID 546960044-Hydroxy-2(1H)-pyridinone

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A 2.49 g quantity of carbomethoxymethylisocyanate was added to a suspension of 2.00 g of 4-hydroxy-2(1H)-pyridone in 60 ml of dioxane, and the mixture was stirred at 90° C. for 30 minutes. The solvent was distilled off, and ether was added to the residue. The precipitate thus formed was filtered, giving 2.20 g of the title compound in a yield of 54%.

Workup

  1. distillationThe solvent was distilled off
  2. additionether was added to the residue
  3. customThe precipitate thus formed
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-a19a7f6eb35a447aba18463ca8449654
Source dataset
uspto-grants-1989_09
Patent number
US04864021

Reaction notes

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