Ammonia → N-(Aminocarbonyl)methacrylamide

HRID 2107544Notes

Reaction equation

HRID 2107544 reaction equation
[NH3:1].C(Cl)(Cl)Cl.[C:6]([N:11]=[C:12]=[O:13])(=[O:10])[C:7]([CH3:9])=[CH2:8]>ClCCCl>[C:6]([NH:11][C:12]([NH2:1])=[O:13])(=[O:10])[C:7]([CH3:9])=[CH2:8]

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 6212Chloroform3×HCID 10942374Methacryloyl isocyanate

Product 1

HCID 88613N-(Aminocarbonyl)methacrylamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Gaseous ammonia was blown into dry chloroform (50 g) to prepare a chloroform solution containing ammonia (0.18 g; 10.5 mmol). To the resultant solution, a solution of methacryloyl isocyanate (1.11 g; 10 mmol) in 1,2-dichloroethane (2 ml) was dropwise added under nitrogen stream while cooling with ice. After completion of the addition, chloroform and 1,2-dichloroethane were evaporated under reduced pressure to give 1-methacryloylurea (1.28 g), which was recrystallized from a mixture of benzene and hexane to give colorless needles. M.P., 137°-138° C.

Workup

  1. temperaturewhile cooling with ice
  2. customwere evaporated under reduced pressure

Sources & evidence

ORD record
ord-7dd219cabded4f7f9700ac592115d8fc
Source dataset
uspto-grants-1990_06
Patent number
US04935413

Reaction notes

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