Triethylamine → N-(3-Methacrylamidopropyl)-3-oxobutanamide

HRID 1975290Notes

Reaction equation

HRID 1975290 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:18])[C:15]([CH3:17])=[CH2:16].[CH2:19]=[C:20]1[O:24][C:22](=[O:23])[CH2:21]1>CO>[C:22]([NH:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:18])[C:15]([CH3:17])=[CH2:16])(=[O:23])[CH2:21][C:20]([CH3:19])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12661DiketeneHCID 103750052-Propenamide, N-(3-aminopropyl)-2-methyl-, hydrochloride (1:1)

Product 1

HCID 23223314N-(3-Methacrylamidopropyl)-3-oxobutanamideYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (24 g, 0.24 mole) was added dropwise at 0° C. to a solution of N-(3-aminopropyl)methacrylamide hydrochloride (40 g, 0.24 mole) and diketene (20 g, 0.24 mole) in methanol (800 ml). After addition, the temperature was maintained at 0° C. for 2 hours under stirring. Stirring was continued at 20° C. for 20 hours. The solvent was then removed. The residue was dissolved in chloroform (1 liter), washed with 5% hydrochloric acid (200 ml), washed with saturated NaHCO3 (200 ml), dried over anhydrous magnesium sulfate, and filtered. Excess solvent was removed. The residue was recrystallized from benzene (500 ml) and ethyl ether (500 ml) to give N-(3-acetoacetamidopropyl)methacrylamide (melting point =93°-94° C.) at a yield of 50%.

Workup

  1. additionAfter addition
  2. stirringStirring
  3. customThe solvent was then removed
  4. dissolutionThe residue was dissolved in chloroform (1 liter)
  5. washwashed with 5% hydrochloric acid (200 ml)
  6. washwashed with saturated NaHCO3 (200 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customExcess solvent was removed
  10. customThe residue was recrystallized from benzene (500 ml) and ethyl ether (500 ml)

Sources & evidence

ORD record
ord-e92361f7cd34477a85de43f7fab61ffd
Source dataset
uspto-grants-1994_02
Patent number
US05286450

Reaction notes

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