Sodium Methoxide → HCID 178512709, Verbindung

Reaktionsgleichung

C[O-].[Na+].Cl.Cl.[NH:6]([C:10]1[S:11][CH:12]=[C:13]([CH2:15][S:16][CH2:17][CH2:18][NH2:19])[N:14]=1)[C:7]([NH2:9])=[NH:8].CO[C:22]1[C:26](OC)=[N:25][S:24](=[O:29])[N:23]=1>CO>[NH:6]([C:10]1[S:11][CH:12]=[C:13]([CH2:15][S:16][CH2:17][CH2:18][NH:19][C:22]2[C:26]([NH:19][CH2:18][CH2:17][S:16][CH2:15][C:13]3[N:14]=[C:10]([NH:6][C:7]([NH2:9])=[NH:8])[S:11][CH:12]=3)=[N:25][S:24](=[O:29])[N:23]=2)[N:14]=1)[C:7]([NH2:9])=[NH:8]

Komponenten

Versuchsvorschrift

To a solution of sodium methoxide (2.16 g; 40.0 mmoles) in 100 ml of CH3OH that was cooled to 0° in an ice-water bath was added 2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine dihydrochloride (6.09 g; 20.0 mmoles) and, after 20 minutes of stirring, the solution was treated with 3,4-dimethoxy-1,2,5-thiadiazole 1-oxide (1.62 g; 10 mmoles). The reaction mixture was stirred at ambient temperature for 65 hours and evaporated under reduced pressure. The residue was chromatographed on 100 g of silica gel (230-400 mesh) by flash chromatography using a gradient elution of acetonitrile-methanol. The appropriate fractions were combined, evaporated and the residue chromatographed on a Preparative HPLC system using μ-porasil silica gel. The appropriate fractions were combined, and evaporated under reduced pressure to give the title compound as an amorphous solid; the NMR spectrum (100 MHz) in d6 dimethyl sulfoxide showed the presence of approximately 0.11 mole of ethanol.