Chemical Properties
Yellow-brown solid
Uses
Nithiamide is a drug for chemotherapy. A protistocide drug with antibacterial activity.
Uses
antiinflammatory, glucocorticoid
Definition
ChEBI: Aminitrozole is an aromatic amide and a member of acetamides.
Safety Profile
Poison by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of SO, and NOx,.
Synthesis
General method: 2-amino-5-nitrothiazole (0.3 g, 2.0 mmol) was dissolved in dichloromethane, followed by the addition of 1.2 molar equivalents of triethylamine (TEA). The reaction mixture was stirred at 5 °C for 15 min, then acetic anhydride (10.0 mmol, 5 eq.) or the corresponding chloride (2.2 mmol, 1.1 eq.) was added slowly and dropwise. The reaction mixture was continued to be stirred at room temperature for 4 to 24 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue is neutralized with saturated sodium bicarbonate (NaHCO3) solution and the resulting solid is purified by recrystallization from the appropriate solvent mixture.
Purification Methods
Recrystallise acinitrazole from EtOH or AcOH. [Hurd & Wehrmeister J Am Chem Soc 71 4007 1949, Beilstein 27 III/IV 4676.]
References
[1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 5, p. 1626 - 1633
