- Sulfonamide (chemistry)
chemistry, the sulfonamide functional group(also spelt sulphonamide ) is -S(=O)2-NH2, a sulfonylgroup connected to an aminegroup.
A sulfonamide (compound) is a compound that contains this group. The general formula is RSO2NH2, where R is some organic group. For example, "methanesulfonamide" is CH3SO2NH2. Any sulfonamide can be considered as derived from a
sulfonic acidby replacing a hydroxylgroup with an amine group.
medicine, the term "sulfonamide" is sometimes used as a synonym for sulfa drug, a derivative or variation of sulfanilamide.
Sulfonamides can be prepared in the laboratory in many ways. For example:
* The reaction of sulfonyl chlorides with
amines in the synthesis of sulfonylmethylamide[ Organic Syntheses, Coll. Vol. 4, p.943 (1963); Vol. 34, p.96 (1954). [http://www.orgsynth.org/orgsyn/prep.asp?prep=cv4p0943 Online Article] ] . A readily available sulfonyl chloride source is tosyl chloride[ Organic Syntheses, Coll. Vol. 5, p.39 (1973); Vol. 48, p.8 (1968). [http://www.orgsynth.org/orgsyn/prep.asp?prep=cv5p0039 Online Article] ] .
* Symmetric sulfonamides are prepared directly from
amines and sulfur dioxidegas ["Sulfamides and sulfamide polymers directly from sulfur dioxide" Alexander V. Leontiev, H. V. Rasika Dias and Dmitry M. Rudkevich Chem. Commun., 2006, 2887 - 2889, DOI|10.1039/b605063h] : :
In this example, the reactants are
aniline, triethylamine, and iodine. Sulfur dioxide is believed to be activated through a series of intermediates: Et3N-I+-I-, Et3N-I+-I3- and Et3N+-SO2-.
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