A new method for synthesis of N,N-diethyl-m-methylbenzamide
Introduction: N, N-diethyl-m-methylbenzamide or N, N-diethyl-m-toluamide (DEET), is well known as an insect repellent. In addition, it is used to improve the dermal and transdermal delivery of many drugs. Objectives: To present a feasible procedure to synthesize DEET from m-toluic acid and diethylam...
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| Main Authors: | , , , , |
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| Format: | Article |
| Language: | Spanish |
| Published: |
ECIMED
2021-12-01
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| Series: | Revista Cubana de Medicina Militar |
| Subjects: | |
| Online Access: | https://revmedmilitar.sld.cu/index.php/mil/article/view/1523 |
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| Summary: | Introduction: N, N-diethyl-m-methylbenzamide or N, N-diethyl-m-toluamide (DEET), is well known as an insect repellent. In addition, it is used to improve the dermal and transdermal delivery of many drugs.
Objectives: To present a feasible procedure to synthesize DEET from m-toluic acid and diethylamine.
Methods: The m-toluic acid was activated with 1,1'-carbonyl-diimidazole, to obtain the intermediate product 1- (m-toluoyl) imidazole that continues to react with diethylamine, to produce DEET. In this way, the factors affecting the synthesis of N, N-diethyl-m-toluamide are improved.
Results: DEET was obtained through an optimal procedure. The by-products of the reaction are soluble in water; they are easily removed by the liquid-liquid extraction method with water and dichloromethane. Most of the DEET obtained has high purity. The yields were 94 to 95 %.
Conclusions: An improved route has been provided for a simple and efficient synthesis of DEET from m-toluic acid and diethylamine in the presence of 1,1'-carbonyl-diimidazole. The synthesis procedure was carried out in one-pot, and the isolation of DEET was achieved by liquid-liquid extraction. The total procedure time was significantly reduced. This synthesis method is easily scalable and industrially feasible. |
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| ISSN: | 1561-3046 |