Acetamide → 1-Methacryloyl-3-acetylurea

HRID 1707508Notes

Reaction equation

HRID 1707508 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-aed5a4ca71cf4043bd2e901b2d190a81
Source dataset
uspto-grants-1994_10
Patent number
US05354495

Reaction notes

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