Acetonitrile → HCID 22557376, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (0.1 mol) was added dropwise at −70° C. under N2 flow to a solution of N,N-dimethylethanamine (0.1 mol) in THF (100 ml). The mixture was stirred at −20° C. for 30 minutes and cooled again to −70° C. Acetonitrile (0.1 mol) was added dropwise. The mixture was stirred at −20° C. for 1 hour and cooled again to −70° C. A solution of 2-[3,5-dichloro-4-(4-chlorobenzoyl)phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (0.05 mol) in THF (100 ml) was added dropwise. The mixture was stirred at −70° C. for 1 hour, then poured out into NH4Cl 10% and extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2). Two pure fractions were collected and their solvents were evaporated, yielding 1.62 g (8%) of (±)-2,6-dichloro-α-(4-chlorophenyl)-4-[4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl]-α-hydroxybenzenepropanenitrile (compound 122).

Provenance & Evidence