Hydrochloric Acid → Ethyl (2-methylacryloyl)carbamate

HRID 1647937Notes

Reaction equation

HRID 1647937 reaction equation
[C:1]([NH2:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[OH-].[Na+].Cl[C:10]([O:12][CH2:13][CH3:14])=[O:11].Cl>O1CCOCC1.O>[C:1]([NH:6][C:10](=[O:11])[O:12][CH2:13][CH3:14])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6595MethacrylamideHCID 10928Ethyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 13628540Ethyl (2-methylacryloyl)carbamateYield 93.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

In 100 g of dioxane, 10 g of methacrylamide and 14.4 g of sodium hydroxide were dissolved and the solution was stirred for 30 minutes at 25°-27° C. Then, 16.6 g of ethyl chloroformate was dissolved in 30 g of dioxane and the solution was added dropwise to the reaction mixture in 3 hours while keeping the reaction temperature of 25° to 30° C. After stirring the solution for 20 minutes, water was added thereto and the solution was neutralized with conc. hydrochloric acid. The solution was extracted with chloroform and the extractant was evaporated in vacuo. The crude product was subjected to NMR assay and 17.2 g of ethyl N-methacryloylcarbamate was isolated.

Workup

  1. additionthe solution was added dropwise to the reaction mixture in 3 hours
  2. customthe reaction temperature of 25° to 30° C
  3. stirringAfter stirring the solution for 20 minutes
  4. extractionThe solution was extracted with chloroform
  5. customthe extractant was evaporated in vacuo

Sources & evidence

ORD record
ord-d9ef3830c8674136a698adc87ae4795a
Source dataset
uspto-grants-1995_07
Patent number
US05434296

Reaction notes

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