Acetamide → 1-Methacryloyl-3-acetylurea

HRID 2107547Notes

Reaction equation

HRID 2107547 reaction equation
[C:1]([NH2:4])(=[O:3])[CH3:2].[C:5]([N:10]=[C:11]=[O:12])(=[O:9])[C:6]([CH3:8])=[CH2:7]>ClCCCl>[C:5]([NH:10][C:11]([NH:4][C:1](=[O:3])[CH3:2])=[O:12])(=[O:9])[C:6]([CH3:8])=[CH2:7]

Participants

4

Reactant 2

HCID 178AcetamideHCID 10942374Methacryloyl isocyanate

Product 1

HCID 136512261-Methacryloyl-3-acetylureaYield 95.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of acetamide (0.59 g; 10 mmol) in 1,2-dichloroethane (20 ml), a solution of methacryloyl isocyanate (1.11 g; 10 mmol) in 1,2-dichloroethane (5 ml) was dropwise added at room temperature, and the reaction mixture was stirred at 80° C. for 3.5 hours. After cooling, 1,2-dichloroethane was evaporated under reduced pressure to give 1-methacryloyl-3-acetylurea (1.63 g), which was recrystallized from a mixture of benzene and hexane to give colorless needles. M.P., 92°-94° C.

Workup

  1. temperatureAfter cooling
  2. custom1,2-dichloroethane was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8b2bda1d0e2448b9b0ea99715459eac2
Source dataset
uspto-grants-1990_06
Patent number
US04935413

Reaction notes

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