Sulfamide
{{Short description|Organosulfur compound}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470473252
| Reference = Merck Index, 11th Edition, 8894.
| ImageFile = sulfamide.png
| ImageSize =
| ImageFile1 = Sulfamide molecule ball.png
| ImageAlt1 = Ball-and-stick model of the sulfamide molecule
| PIN= Sulfamide
|IUPACName=Sulfuric diamide
| OtherNames = Sulphamide
Sulfuryl amide
|Section1={{Chembox Identifiers
| Abbreviations =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 74243
| InChI = 1/H4N2O2S/c1-5(2,3)4/h(H4,1,2,3,4)
| InChIKey = NVBFHJWHLNUMCV-UHFFFAOYAV
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 355001
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/H4N2O2S/c1-5(2,3)4/h(H4,1,2,3,4)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NVBFHJWHLNUMCV-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 7803-58-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = VS7TZW634V
| EINECS =
| PubChem = 82267
| SMILES = O=S(=O)(N)N
| RTECS =
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| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 29368
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG =
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|Section2={{Chembox Properties
| Formula = {{chem2|H4N2O2S}}
| MolarMass = 96.11 g/mol
| Appearance = White orthorhombic plates
| Density =
| MeltingPtC = 93
| MeltingPt_notes =
| BoilingPtC = 250
| BoilingPt_notes = (decomposes)
| Solubility = Freely soluble
| SolubleOther =
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| MagSus = −44.4{{x10^|-6}} cm3/mol }}
|Section7={{Chembox Hazards
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Sulfamide (IUPAC name: sulfuric diamide) is a compound with the chemical formula {{chem2|SO2(NH2)2}} and structure {{chem2|H2N\sS(\dO)2\sNH2}}. Sulfamide is produced by the reaction of sulfuryl chloride with ammonia. Sulfamide was first prepared in 1838 by the French chemist Henri Victor Regnault.Regnault, Victor (1838) [https://books.google.com/books?id=oSdCAAAAcAAJ&pg=PA170 "Sur l'acide chlorosulfurique et la sulfamide"] (On sulfuryl chloride and sulfamide), {{lang|fr|Annales de chimie et de physique}}, series 2, 69 : 170-184; see especially "{{lang|fr|Action de gaz ammoniac sec sur la liqueur chlorosulfurique}}" (Action of dry ammonia gas on liquid sulfuryl chloride), pages 176-180.
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:{{cite journal | last1 = Leontiev | first1 = A. V. | last2 = Dias | first2 = H. V. R. | last3 = Rudkevich | first3 = D. M. | title = Sulfamides and sulfamide polymers directly from sulfur dioxide | journal = Chemical Communications | year = 2006 | volume = 2006 | issue = 27 | pages = 2887–2889 | doi = 10.1039/b605063h | pmid = 17007406 }}
:Image:SulfonamideSynthesisfromSO2.png
In this example, the reactants are aniline, triethylamine ({{chem2|Et3N}}, Et = ethyl group), and iodine. Sulfur dioxide is believed to be activated through a series of intermediates: {{chem2|Et3N\s+\sI-}}, {{chem2|Et3N\sI+\sI3-}} and {{chem2|Et3N+\sSO2-}}.
The sulfamide functional group is an increasingly common structural feature used in medicinal chemistry.{{cite journal |author1=Reitz, A. B. |author2=Smith, G. R. |author3=Parker, M. H. | title = The Role of Sulfamide Derivatives in Medicinal Chemistry: A Patent Review (2006 – 2008) | journal = Expert Opinion on Therapeutic Patents | year = 2009 | volume = 19 | issue = 10 | pages = 1449–1453 | doi = 10.1517/13543770903185920 | pmid = 19650745 |s2cid=6561685 }}