Acetamide → 1-Methacryloyl-3-acetylurea

HRID 2107548Notes

Reaction equation

HRID 2107548 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.N1C=CC=CC=1>[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

5

Reactant 2

HCID 178AcetamideHCID 10942374Methacryloyl isocyanate

Product 1

HCID 136512261-Methacryloyl-3-acetylureaYield 79.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 111,2-DichloroethaneSolvent2×

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 (10 ml) was dropwise added. After completion of the addition, pyridine (5 drops) was added to the solution, and then stirring was continued at room temperature for 12 hours. 1,2-Dichloroethane was evaporated under reduced pressure to give 1-methacryloyl-3-acetylurea (1.36 g), which was recrystallized from a mixture of benzene and hexane to give colorless needles. M.P., 92°-94° C.

Workup

  1. additionwas added to the solution
  2. custom1,2-Dichloroethane was evaporated under reduced pressure

Sources & evidence

ORD record
ord-aab8c526791648f7ac6d8aed228b77f0
Source dataset
uspto-grants-1990_06
Patent number
US04935413

Reaction notes

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