Sulfamide
chemical compound
Sulfamide (IUPAC name: sulfuric diamide) is a compound with the chemical formula SO2(NH2)2 and structure H2N−S(=O)2−NH2.
Sulfamide was first prepared in 1838 by the French chemist Henri Victor Regnault. It is produced by the reaction of sulfuryl chloride with ammonia. The process generally gives only about 50% sulfamide, "with the remaining products being imidodisulphamide, HN(SO2NH2)2 and other longer-chain and cyclic condensation products."
Sulfamide functional group
In organic chemistry, the term sulfamide may also refer to the functional group which consists of at least one organic group attached to a nitrogen atom of sulfamide.
Symmetric sulfamides can be prepared directly from amines, sulfur dioxide gas and an oxidant:
In this example, the reactants are aniline, triethylamine (Et3N, Et = ethyl group), and iodine. Sulfur dioxide is believed to be activated through a series of intermediates: Et3N−+−I−, Et3N−I+−I−3 and Et3N+−SO−2.
The sulfamide functional group is an increasingly common structural feature used in medicinal chemistry.
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This entry incorporates text from “Sulfamide” on English Wikipedia. Contributors are listed in the page history. Text is available under the Creative Commons Attribution-ShareAlike 4.0 License. Selected authority identifiers and statements are retrieved from Wikidata under CC0; their references and qualifiers remain part of the verification path.