Sulfonamide (chemistry)
In chemistry, the sulfonamide functional group (also spelt sulphonamide) is -S(=O)2-NH2, a sulfonyl group connected to an amine group.
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 acid by replacing a hydroxyl group with an amine group.
In medicine, the term "sulfonamide" is sometimes used as a synonym for sulfa drug, a derivative or variation of sulfanilamide.
Organic synthesis
Sulfonamides can be prepared in the laboratory in many ways. For example, by the reaction of sulfonyl chlorides with amines in the synthesis of sulfonylmethylamide.[1] A readily available sulfonyl chloride source is tosyl chloride.[2]
Triflimide or triflimidic acid HN(Tf)2 (bis(trifluoromethane)sulfonimide) is the formal adduct of triflic acid and ammonia. Phenyl triflimide is a triflating reagent. The related metal triflimidates are used as catalysts. The anion bistriflimide is hydrophobic.
Sulfinamides
The related sulfinamides (R(S=O)NHR) are amides of sulfinic acids (R(S=O)OH) (see sulfinyl). Chiral sulfinamides such as tert-butanesulfinamide, p-toluenesulfinamide [3][4] and 2,4,6-trimethylbenzenesulfinamide [5] are relevant to asymmetric synthesis.
References
- ^ Organic Syntheses, Coll. Vol. 4, p.943 (1963); Vol. 34, p.96 (1954). Online Article
- ^ Organic Syntheses, Coll. Vol. 5, p.39 (1973); Vol. 48, p.8 (1968). Online Article
- ^ Organic Syntheses, Coll. Vol. 10, p.47 (2004); Vol. 77, p.50 (2000). Link
- ^ Org. Synth 2007, 84, 129-138 Link
- ^ Org. Synth. 2006, 83, 131-140 Link
