Sulfamide
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| Names | |
|---|---|
| IUPAC name
Sulfuric diamide | |
| Other names
Sulphamide Sulfuryl amide | |
| Identifiers | |
7803-58-9  | |
| ChEBI | CHEBI:29368  |
| ChEMBL | ChEMBL355001 |
| ChemSpider | 74243 |
| |
| Jmol-3D images | Image |
| PubChem | 82267 |
| |
| Properties | |
| H4N2O2S | |
| Molar mass | 96.11 g/mol |
| Appearance | White orthorhombic plates |
| Melting point | 93 °C (199 °F; 366 K) |
| Boiling point | 250 °C (482 °F; 523 K) (decomposes) |
| Freely soluble | |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| verify (what is: /?) | |
| Infobox references | |
Sulfamide (IUPAC name: sulfuric diamide) is a chemical compound with the molecular structure H2NSO2NH2. Sulfamide is produced by the reaction of sulfuryl chloride with ammonia. Sulfamide was first prepared in 1838 by the French chemist Henri Victor Regnault.[2]
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 and sulfur dioxide gas:[3]
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−.
The sulfamide functional group is an increasingly common structural feature used in medicinal chemistry.[4]
See also
References
- ↑ Merck Index, 11th Edition, 8894.
- ↑ Regnault, Victor (1838) "Sur l'acide chlorosulfurique et la sulfamide" (On sulfuryl chloride and sulfamide), Annales de chimie et de physique, series 2, 69 : 170-184; see especially "Action de gaz ammoniac sec sur la liqueur chlorosulfurique" (Action of dry ammonia gas on liquid sulfuryl chloride), pages 176-180.
- ↑ Leontiev, A. V.; Dias, H. V. R.; Rudkevich, D. M. (2006). "Sulfamides and sulfamide polymers directly from sulfur dioxide". Chemical Communications 2006 (27): 2887–2889. doi:10.1039/b605063h.
- ↑ Reitz, A. B.; Smith, G. R.; Parker, M. H. (2009). "The Role of Sulfamide Derivatives in Medicinal Chemistry: A Patent Review (2006 – 2008)". Expert Opinion on Therapeutic Patents 19 (10): 1449–1453. doi:10.1517/13543770903185920. PMID 19650745.