Triethylamine → HCID 10370874, compound

Participants

Reaction Steps

2'-Methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxylic acid (E. P. 0533268A 1) (0.212 g, 0.721 mmol) was suspended in dichloromethane (5 ml) and treated with oxalyl chloride (0.094 ml, 1.08 mmol), followed by a drop of dry DMF with stirring. After 4 h, the reaction mixture was evaporated under reduced pressure and dried in vacuo to give the crude acid chloride as a yellow solid. Meanwhile to a solution of the product from description 2 (0.142 g, 0.683 mmol) in dichloromethane (10 ml); triethylamine (0.095 ml, 0.683 mmol) was added, followed by a solution of the crude acid chloride in dichloromethane (4 ml), with stirring. After 1 h, the reaction mixture was washed with water (1×), followed by sodium bicarbonate solution (1×). The organic layer was then dried (Na2SO4) and evaporated under reduced pressure to give a brown oil which was dried in vacuo. The oil was purified by SiO2 chromatography (7.5% MeOH in CH2Cl2 as eluant) to give the title compound as a pale yellow oil (0.052 g, 16%) which was converted to its oxalate salt. m.pt 144°-148° C. (oxalate salt)

Provenance & Evidence