Hydrochloric Acid → Ethyl (2-methylacryloyl)carbamate

HRID 1647934Notes

Reaction equation

HRID 1647934 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 18.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

In 41 g of dioxane, 2.5 g of methacrylamide and 1.18 g of NaOH were dissolved and the solution was stirred for 1.0 hour at the temperature of 25° to 27° C. Then, 4.0 g of ethyl chloroformate was dissolved in 10 g of dioxane and the solution was added to the reaction mixture at once. After stirring the solution for 15 minutes, water was added thereto and the solution was neutralized by adding conc. hydrochloric acid and filtered. The filtrate was extracted with chloroform and the extract was evaporated in vacuo. The crude product was subjected to column chromatography for purification, thereby obtaining 0.841 g of ethyl N-methacryloylcarbamate. Melting point (mp.) of the compound was 73°-74° C.

Workup

  1. additionthe solution was added to the reaction mixture at once
  2. stirringAfter stirring the solution for 15 minutes
  3. filtrationfiltered
  4. extractionThe filtrate was extracted with chloroform
  5. customthe extract was evaporated in vacuo
  6. customThe crude product was subjected to column chromatography for purification

Sources & evidence

ORD record
ord-ec93e59eb75b46d3acdd3412881dbfc0
Source dataset
uspto-grants-1995_07
Patent number
US05434296

Reaction notes

Loading…