Potassium Sodium Tartrate → HCID 178444049, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3,4-diaminobenzonitrile (1.08 g, 8.10 mmol) in THF (20 mL) at 0° C. was added trimethylaluminum (4.86 mL, 9.72 mmol, 2 M in hexanes). After 10 min, methyl 2-(4-(heptyloxy)phenyl)acetate (2.36 g, 8.91 mmol) was added and the cooling bath removed. After stirring for 48 h at 60° C., the reaction mixture was allowed to cool to room temperature then poured into a mixture of Rochelle's salt (6.86 g, 24.31 mmol) in water (150 mL) and EA (100 mL) and stirred for 2 h. The layers were split and the aqueous layer further extracted with EA (50 mL). The combined organics were washed successively with water (100 mL) and brine (50 mL), dried over MgSO4 and evaporated. The residue was taken up in xylenes (50 mL), treated with toxic acid (0.154 g, 0.810 mmol) and heated under reflux for 18 h. The reaction mixture was allowed to cool, diluted with EA (100 mL), washed with NaHCO3 (100 mL), dried over MgSO4 and evaporated. The crude material was purified by chromatography (EA/isohexanes) then re-slurried from isohexanes to afford 2.19 g, (78%) of 2-(4-(heptyloxy)benzyl)-1H-benzo[d]imidazole-5-carbonitrile as a white solid INT-46. LCMS-ESI (m/z) calculated for C22H25N3O: 347; found 348 [M+H]+, tR=2.82 min (Method 5).

Provenance & Evidence