Hydrochloric Acid → Ethyl (2-methylacryloyl)carbamate

HRID 2082195Notes

Reaction equation

HRID 2082195 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-e2bd88a370714922b4e320595faa08bc
Source dataset
uspto-grants-1993_02
Patent number
US05187306

Reaction notes

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