lab report on synthesis and characterization of N,N-diethyl-3-methylbenzamide (DEET)

May 5th, 2015
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American Institute of Medical Technology
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N,N-diethyl-3-methylbenzamide (DEET) was synthesized by using COMU as a activating agent . mechanism difference between the DCC /DMAP and COMU , DEAD /PPh3

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ABSTRACT: N,N-diethyl-3-methylbenzamide (DEET) was Asuccessfully synthesized with high yield by using a novel procedure,in which COMU [(1-cyano-2- ethoxy-2oxoethylidenaminooxy)dimethylamino-morpholino-carbeniumhexafluorophosphate], was used as a nonhazardous partner, in the onepot coupling of a carboxylic acid and amine producing. As we know thatthe carboxylic acid is not act as an electrofile like aldehyde or ketone.So by keeping in mind the fundamental principles of carbonyl reactivitythis reaction was carried out in the laboratory, with potential forexpansion to new methods of amide bond formation. The reaction wasmonitored visually by virtue of the color change during the course ofreaction, conveniently all the byproducts are water-soluble, and DEET isnot water soluble so easily separation of the compound from the byproduct and confirmed by HNMR.Introduction:N,N-diethyl-3-methylbenzamide is slightly yellow oil. It was developedby the military as an insect repellent in 1946 and introduced for publicuse in 1957. It has broad-spectrum activity its effectively repels mostbiting flies mosquitoes, chiggers, fleas and ticks also for other diseasecarrying insects. Lack of eclectofilcity of carboxylic acid functionalgrope that creates problem in simple coupling reaction which can besolved by converting acid to acid chloride. But there are too muchdisadvantage of this reaction people generally uses thionyl chloride,oxalyl chloride and phosphorus trichloride as

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