Hydrochloric Acid → Ethyl (2-methylacryloyl)carbamate

HRID 2082196Notes

Reaction equation

HRID 2082196 reaction equation
[C:1]([NH2:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[O-]CC.[Na+].Cl[C:12]([O:14][CH2:15][CH3:16])=[O:13].Cl>O1CCOCC1>[C:1]([NH:6][C:12](=[O:13])[O:14][CH2:15][CH3:16])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6595MethacrylamideHCID 10928Ethyl chloroformateHCID 2723922Sodium ethoxide

Product 1

HCID 13628540Ethyl (2-methylacryloyl)carbamateYield 7.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
27 °C

Procedure

In 52 g of dioxane, 12.5 g of methacrylamide and 1.0 g of sodium ethoxide (NaOEt) were dissolved and the solution was stirred for 20 minutes at the temperature of 27° C. Then, 4.0 g of ethyl chloroformate acid was dissolved in 2 g of dioxane and the solution was added in two portions into the above reaction solution. After leaving it for one day, the solution was neutralized with conc. hydrochloric acid and was extracted with chloroform. The extract was evaporated in vacuo. The crude product was subjected to column chromatography, thereby obtaining 0.44 g of ethyl N-methacryloylcarbamate. Melting point of the compound was 73°-74° C.

Workup

  1. additionthe solution was added in two portions into the above reaction solution
  2. customAfter leaving it for one day
  3. extractionwas extracted with chloroform
  4. customThe extract was evaporated in vacuo

Sources & evidence

ORD record
ord-c108471dad5a4696b91b7ed916bc0a73
Source dataset
uspto-grants-1993_02
Patent number
US05187306

Reaction notes

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