Carbamic acid, ethyl ester → Ethyl (2-methylacryloyl)carbamate

HRID 2082200Notes

Reaction equation

HRID 2082200 reaction equation
[C:1](=[O:6])([O:3][CH2:4][CH3:5])[NH2:2].[H-].[Na+].[C:9](Cl)(=[O:13])[C:10]([CH3:12])=[CH2:11]>CC1C=CC=CC=1C>[C:9]([NH:2][C:1](=[O:6])[O:3][CH2:4][CH3:5])(=[O:13])[C:10]([CH3:12])=[CH2:11]

Participants

5

Reactant 3

HCID 5641Carbamic acid, ethyl esterHCID 13528Methacryloyl chlorideHCID 24758Sodium hydride

Product 1

HCID 13628540Ethyl (2-methylacryloyl)carbamateYield 38.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent3×

Conditions

Temperature
50 °C

Procedure

To the solution of 8.9 g of ethyl carbamate in 50 g of o-xylene, a slurry of 2.2 g of NaH in 20 g of xylene was added dropwise in 30 minutes, followed by stirring for additional 3 hours at 50° C. Then a solution of 10.5 g of methacryloyl chloride in 30 g of xylene was added dropwise to the reaction mixture and the solution was stirred for 1 hour at 60° C. The resultant white precipitate were filtered off and the filtrate was concentrated. The residue was subjected to column chromatography for purification, thereby obtaining 6.1 g of ethyl N-methacryloylcarbamate.

Workup

  1. stirringthe solution was stirred for 1 hour at 60° C
  2. filtrationThe resultant white precipitate were filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue was subjected to column chromatography for purification

Sources & evidence

ORD record
ord-3fe3bcbd71a24c8fbd9b720db8a69ee3
Source dataset
uspto-grants-1993_02
Patent number
US05187306

Reaction notes

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