2-Propanol, reaction products with ammonia, distn. residues → HCID 21082062, compound

Participants

Reaction Steps

NH3/iPrOH saturated solution (40 ml) was added dropwise at 0° C. to a solution of 7-[chloro(4-chlorophenyl)[4-methyl-5-(methylthio)-4H-1,2,4triazol-3-yl)methyl]-5-(3-chlorophenyl)-tetrazolo[1,5-a)quinazoline (0.0036 mol) in THF (80 ml). The mixture was stirred from 0° C. to room temperature then at room temperature for 2 hours, poured out into ice water and extracted with EtOAc. The organic layer was separated, washed with water, dried (MgSO4), filtered and the solvent was evaporated. The residue (2 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH; 98/2/0.1; 15–40 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.35 g (18%) of 5-(3-chlorophenyl)-α-(4-chlorophenyl)-α-[4-methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl]-tetrazolo[1,5-a]quinazoline-7-methanamine. A sample (0.15 g) was crystallized from CH3CN/diethyl ether. The precipitate was filtered off and dried, yielding 0.05 g of 5-(3-chlorophenyl)-α-(4-chlorophenyl)-α-[4methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl]-tetrazolo[1,5-a]quinazoline-7-methanamine, mp. 150° C.

Provenance & Evidence