2-aminoethanesulphonamide monohydrochloride Chemical Properties

Melting point:

133 °C

Boiling point:

315°

Flash point:

150°

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)

form 

Solid

color 

White to Off-White

InChI

InChI=1S/C2H8N2O2S.ClH/c3-1-2-7(4,5)6;/h1-3H2,(H2,4,5,6);1H

InChIKey

DGUVEYAZTOUCEJ-UHFFFAOYSA-N

SMILES

C(S(N)(=O)=O)CN.[H]Cl

2-aminoethanesulphonamide monohydrochloride Usage And Synthesis

Description

2-Aminoethanesulphonamide monohydrochloride is a perovskite with a hexagonal shape. It has been shown to interact with the pharmacophore of the enzyme cytochrome P450, and it has been optimized for the reaction by altering its structure. This product is soluble in gaseous form, but can also be used as a solid. 2-Aminoethanesulphonamide monohydrochloride has an absorption maximum at 325 nm and emits fluorescence at 420 nm. It is used in devices that detect ionizing radiation.

Uses

Taurinamide is a derivative of Taurolidine; a drug with antimicrobial and antiendotoxic properties.

Synthesis

General Method B: Deprotection of phthalimidosulfonamides to prepare the corresponding primary amines. The following procedure applies to the synthesis of aminoethanesulfonamides or aminopropanesulfonamides. The synthesis of 2-aminoethanesulfonamide hydrochloride from 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethanesulfonamide was carried out as follows: 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethanesulfonamide (1.52 g, 6.78 mmol) was suspended in ethanol (30 ml), and refluxed by heating. Subsequently, 64% hydrazine hydrate solution (0.36 ml, 7.5 mmol) was slowly added to the reaction system. After 3 hours of reaction, precipitate generation was observed and the precipitate was removed by filtration. The filtrate was concentrated to dryness and the residue was dissolved in water (150 ml). The aqueous phase suspension was acidified with concentrated hydrochloric acid and filtered to remove hydrochloric acid and insoluble impurities. The filtrate was again concentrated to dryness and the crude product was recrystallized by solvent mixing of ethanol/water (9:1) to give 764 mg (64% yield) of the target product 2-aminoethanesulfonamide hydrochloride as a solid. The product was characterized by 1H-NMR (D2O) with chemical shifts δ (ppm) of 3.62-3.55 (m, 2H) and 3.51-3.44 (m, 2H).

References

[1] Patent: EP2077263, 2009, A1. Location in patent: Page/Page column 15-16
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 11, p. 5462 - 5470
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 3, p. 474 - 483

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