Biginelli - stretching of bonds and thereby heating the...

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Amy Linkous 9/30/09 CHEM 2556: CRN: 91653 Biginelli Reaction Objective: To use microwave radiation to drive the amidoalkylation reaction. General Reaction: Procedure: 1.08 g urea, 10 mL ethanol, 2 mL concentrated hydrochloric acid, 2.65 g benzaldehyde and 3.25 g ethyl acetoacetate were combined in a microwave vessel. A magnetic stir bar was added and the mixture was submitted for microwave radiation. After one hour and twenty minutes of microwave radiation the vessel was removed and allowed to cool, then placed in an ice bath to precipitate the product. The solid white product was filtered by suction using a
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Büchner funnel and was washed once with about 3 mL cold ethanol and three times with dichloromethane. The product was recrystallized in ethanol, collected and dried. Data: Yield: 1.603 g Melting point range: 207.6 – 208.8 C 1 H NMR Spectrum:
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Discussion: The use of microwave radiation in the experiment significantly reduces the time required for heating. Microwave radiation causes the molecules to vibrate individually, inducing the
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Unformatted text preview: stretching of bonds and thereby heating the mixture much quicker than conventional reflux heating. Urea undergoes nucleophilic addition to benzaldehyde and condensation (dehydration) occurs. The ethyl acetoacetate adds to the new compound and another condensation occurs in conjunction with ring closure by nucleophilic attack, and the product is formed. Results: The melting point range found for this product is exactly where it should be, according to the literature value of 208 C. The phenyl ring shows up on the NMR, as well as the ester and the amides in the new ring. The carboxylic acid peak is present at almost 1700 and the amide and ester stretches are also present. Conclusion: Given the information gathered from the measured melting point range and the IR and NMR spectra, it is reasonable to conclude that the experiment was successful and the intended product was made....
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This note was uploaded on 02/22/2010 for the course CHEM 2556 at Virginia Tech.

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Biginelli - stretching of bonds and thereby heating the...

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