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==Synthesis== | ==Synthesis== | ||
⚫ | ] | ||
] of substituted ] () followed by ammonolysis of the product gives ] (). The regiochemistry | |||
⚫ | ] | ||
of the next reaction, nucleophilic aromatic displacement, can be attributed in this case to the better leaving group properties of fluoride ions over chloride ions. Reaction with 2-methylaminothiophene () thus gives () as the product. There is ample precedent to indicate that tetrazoles are bioisosteric with carboxylic acids, with the two groups showing quite comparable pKAs. Treatment with ] and ] leads to 1,3 addition of the elements of ] to the nitrile and the formation of a ] ring. This yields the high ceiling diuretic agent '']''. | |||
==References== | ==References== |
Revision as of 08:01, 13 January 2015
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ECHA InfoCard | 100.044.121 |
Chemical and physical data | |
Formula | C12H11ClN6O2S2 |
Molar mass | 370.84 g/mol g·mol |
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Azosemide is a high-ceiling diuretic agent.
Synthesis
Chlorosulfonation of substituted benzonitrile () followed by ammonolysis of the product gives sulfonamide (). The regiochemistry of the next reaction, nucleophilic aromatic displacement, can be attributed in this case to the better leaving group properties of fluoride ions over chloride ions. Reaction with 2-methylaminothiophene () thus gives () as the product. There is ample precedent to indicate that tetrazoles are bioisosteric with carboxylic acids, with the two groups showing quite comparable pKAs. Treatment with sodium azide and hydrochloric acid leads to 1,3 addition of the elements of hydrazoic acid to the nitrile and the formation of a tetrazole ring. This yields the high ceiling diuretic agent azosemide.
References
Popelak, A.; Lerch, A.; Stach, K.; Roesch, E.; Hardebeck, K.; German Offen., 1970, 815922; Chem. Abstr. 1970, 73, 45519.
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