Water → Ethyl [(2-methylacryloyl)amino](oxo)acetate

HRID 1032076Notes

Reaction equation

HRID 1032076 reaction equation
[C:1](Cl)([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2].[C:9]([NH2:14])(=[O:13])[C:10]([CH3:12])=[CH2:11].O>C(Cl)(Cl)Cl>[C:1]([NH:14][C:9](=[O:13])[C:10]([CH3:12])=[CH2:11])([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6595MethacrylamideHCID 20884Ethoxalyl chloride

Product 1

HCID 14298183Ethyl [(2-methylacryloyl)amino](oxo)acetateYield 28.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Into the same reaction vessel as used in Example 1, ethoxalyl chloride (12.3 g; 0.09 mol) was charged, and the reaction vessel was cooled in an ice bath. A solution of methacrylamide (20.3 g; 0.24 mol) in chloroform (90.0 ml) was dropwise added thereto in 30 minutes, followed by stirring at room temperature for 3 days. The reaction mixture was shaken with chloroform (500 ml) and water (500 ml), and the chloroform layer was separated and dried over anhydrous magnesium sulfate, followed by removal of chloroform. Hydroquinone (0.01 g) was added thereto, and distillation under reduced pressure was carried out to give N-ethoxalylmethacrylamide (4.8 g). Yield, 29%.

Workup

  1. additionwas charged
  2. temperaturethe reaction vessel was cooled in an ice bath
  3. customthe chloroform layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customfollowed by removal of chloroform
  6. additionHydroquinone (0.01 g) was added
  7. distillationdistillation under reduced pressure

Sources & evidence

ORD record
ord-bf268c957c4d48caa7a2f735b3cec38e
Source dataset
uspto-grants-1990_09
Patent number
US04956491

Reaction notes

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