Nitrogen → HCID 21082000, compound

Participants

Reaction Conditions

Reaction Steps

N2 was bubbled at room temperature in a solution of 5-(3-chlorophenyl)-α-(4-iodophenyl)-α-(4-methyl-4H-1,2,4-triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanamine (0.0024 mol) in DMF (15 ml) for 1 hour. Zn(CN)2 (0.0036 mol) and Pd(PPh3)4 (0.0002 mol) were added. The mixture was stirred at 80° C. for 1 hour, cooled, poured out into ice water and extracted with EtOAc. The precipitate was filtered off (secondary product). The organic layer was washed twice with water then with saturated NaCl, separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.2 to 80/20/2; 15–35 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.425 g (35%) of 4-[amino[5-(3-chlorophenyl)tetrazolo[1,5-a]quinazolin-7-yl](4-methyl-4H-1,2,4-triazol-3-yl)methyl]-benzonitrile which were crystallized from CH3CN. The precipitate was filtered off and dried, yielding 0.19 g (16%) of 4-[amino[5-(3-chlorophenyl)tetrazolo[1,5-a]quinazolin-7-yl](4methyl-4H-1,2,4-triazol-3-yl)methyl]-benzonitrile, mp. 194° C.

Provenance & Evidence