Sulfate Ion → HCID 178433685, compound

Participants

Reaction Steps

i A solution of n-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]-thiourea (2.29 g) and methyl iodide (1.56 g) in methanol (5 ml) was kept at room temperature for 18 hours affordng S-methyl-N -[2-((5-methyl-4-imidazolyl)methylthio)ethyl] thiouronium iodide (2.3 g), m.p. 128°-131°. The iodide was converted into the corresponding sulphate by ion-exchange on an ion-exchange resin (IRA 401) in the sulphate form. ii. A solution of S-methyl-N-[2-((5-methyl-4-imidazolyl) methylthio)-ethyl] thiouronium sulphate (2.93 g) and 4-(3-aminopropyl) imidazole (1.25 g) in water (10 ml) was heated under reflux for 3 hours. Following concentration, the residue was converted to the free base with an ion-exchange resin (IRA 401) in the OH- form and then applied to a weakly acid cation exchange resin (CG 50 in the H+ form) and eluted with dilute hydrochloric acid. The eluate was concentraed to give the title compound which was isolated as the tripicrate (1.8 g) m.p. 183°-185° (from acetone-water). (Found: C, 37.8; H, 3.2; N,21.8% C14H23N7S.3 C6H3N3O7 requires: C, 38.1; H, 3.2; N,22.2%). The tripicrate was converted into the trihydrochloride salt by means of ion-exchange resin IRA 400 (Cl-). The tripcrate was converted into the free base by means of ion-exchange resin IRA 401 (OH-) and the free base was treated with oxalic acid in warm ethanol. The dioxalate crystallised on cooling and was recrystalised from aqueous etanol m.p. 125°-127°. (Found: C, 42.8; H, 5.4; N, 19.4; S, 6.3; C14H23N7S.2 C2H2O4 requires: C, 43.1; H, 5.4; N, 19.5; S, 6.4%)

Provenance & Evidence