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

HRID 1073658Notes

Reaction equation

HRID 1073658 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].N1C=CC=CC=1.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

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6595MethacrylamideHCID 20884Ethoxalyl chloride

Product 1

HCID 14298183Ethyl [(2-methylacryloyl)amino](oxo)acetateYield 31.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

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 (7.7 g; 0.09 mol) in chloroform (32.4 ml) was dropwise added thereto in 10 minutes. After completion of the addition, a mixture of pyridine (7.2 g; 0.09 mol) and chloroform (10 ml) was added thereto, and the resulting mixture was stirred at room temperature for 1 hour. 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 (5.3 g). Yield, 32%.

Workup

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

Sources & evidence

ORD record
ord-b08356826c2244878bba3529d5b3772b
Source dataset
uspto-grants-1990_11
Patent number
US04970281

Reaction notes

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