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

HRID 1073657Notes

Reaction equation

HRID 1073657 reaction equation
[C:1]([NH2:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:7](Cl)([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:8]>C1C=CC=CC=1>[C:7]([NH:6][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:8]

Participants

4

Reactant 2

HCID 6595MethacrylamideHCID 20884Ethoxalyl chloride

Product 1

HCID 14298183Ethyl [(2-methylacryloyl)amino](oxo)acetateYield 42.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Into a reaction vessel equipped with a stirrer, a cooler, an nitrogen gas introducing inlet and a dropping funnel, benzene (288.5 ml) and methacrylamide (49.1 g; 0.577 mol) were charged, and the resulting mixture was heated with reflux. Refluxing and bubbling with nitrogen gas were continued, during which ethoxalyl chloride (78.5 g; 0.577 mol) was dropwise added thereto in 2.5 hours. After the dropwise addition was completed, refluxing was continued for 5 hours. The benzene was distilled off, hydroquinone (0.01 g) was added thereto, and distillation under reduced pressure was carried out to give N-ethoxalylmethacrylamide (45.8 g). Yield, 43%. B.P., 110-115° C./0.3 mmHg. Refractive index, 1.473.

Workup

  1. customInto a reaction vessel equipped with a stirrer
  2. additiona cooler, an nitrogen gas introducing inlet and a dropping funnel
  3. temperaturethe resulting mixture was heated
  4. temperaturewith reflux
  5. temperatureRefluxing
  6. custombubbling with nitrogen gas
  7. additionwas dropwise added
  8. additionAfter the dropwise addition
  9. temperaturerefluxing
  10. waitwas continued for 5 hours
  11. distillationThe benzene was distilled off
  12. additionhydroquinone (0.01 g) was added
  13. distillationdistillation under reduced pressure

Sources & evidence

ORD record
ord-95395c1ff753489589c39cfe63252450
Source dataset
uspto-grants-1990_11
Patent number
US04970281

Reaction notes

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