Toluene → N-(3,5-Bis(hydroxymethyl)phenyl)-1-((3,4-dichlorophenyl)methyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide

Participants

Reaction Steps

To a solution of dimethyl 5-[({1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}carbonyl)amino]-1,3-benzenedicarboxylate (Intermediate 14) (0.65 g, 1.3 mmol) in THF (40 mL), was added a 1M solution of DIBAL-H in toluene (10 mL, 7 eq) and the reaction was stirred to room temperature for 2 hours. Solid NH4Cl was added and the reaction mixture was stirred at RT for 30 min. The aqueous phase was extracted with ether and AcOEt, dried over sodium sulphate and evaporated. After recrystallisation from acetonitrile, the title compound was obtained as a white solid (240 mg, 44%). HRMS calculated for C19H18Cl2N4O3 (M+H)+421.0834. found: 421.0833, Rt: 2.51 min. MP: 194.5° C.

Provenance & Evidence