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

HRID 67744

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

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 (m.p.=93°-94° C.) at a yield of 50%.

Workup

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

Sources & evidence

ORD record: ord-b568e52c429c41d884e4a5fac2e5a3f6
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04346231

Linked notes

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