Sulfonamide

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The structure of the sulfonamide group

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[edit]

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[edit]

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.

See also[edit]

References[edit]

  1. ^ Organic Syntheses, Coll. Vol. 4, p.943 (1963); Vol. 34, p.96 (1954). Online Article
  2. ^ Organic Syntheses, Coll. Vol. 5, p.39 (1973); Vol. 48, p.8 (1968). Online Article
  3. ^ Organic Syntheses, Coll. Vol. 10, p.47 (2004); Vol. 77, p.50 (2000). Link
  4. ^ Org. Synth 2007, 84, 129-138 Link
  5. ^ Org. Synth. 2006, 83, 131-140 Link