Methylamine → 1-Methacryloyl-3-methylurea

HRID 2107545Notes

Reaction equation

HRID 2107545 reaction equation
[CH3:1][NH2:2].[C:3]([N:8]=[C:9]=[O:10])(=[O:7])[C:4]([CH3:6])=[CH2:5]>C(Cl)(Cl)Cl.ClCCCl>[C:3]([NH:8][C:9]([NH:2][CH3:1])=[O:10])(=[O:7])[C:4]([CH3:6])=[CH2:5]

Participants

5

Reactant 2

HCID 6329Methylamine2×HCID 10942374Methacryloyl isocyanate

Product 1

HCID 136436411-Methacryloyl-3-methylureaYield 99.9%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 6212ChloroformSolvent2×

Procedure

To a solution of methylamine (0.35 g; 11.29 mmol) in chloroform (30 ml), 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, 1,2-dichloroethane and methylamine were evaporated under reduced pressure to give 1-methacryloyl-3-methylurea (1.42 g), which was recrystallized from a mixture of benzene and hexane to give colorless plates. M.P., 112°-113.5° C.

Workup

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

Sources & evidence

ORD record
ord-931aef3f64d140f6bfe355f8f84b5c49
Source dataset
uspto-grants-1990_06
Patent number
US04935413

Reaction notes

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