1,1'-Carbonyldiimidazole → HCID 86583671, compound

Participants

Reaction Steps

To a solution of 2′-amino-3,3″-bis-trifluoromethyl-[1,1′:3′1″]terphenyl-5′-carboxylic acid (0.113 g, 0.27 mmol 1 eq) in DMF (2.7 mL) was added 1,1′-carbonyldiimidazole (0.120 g, 0.74 mmol 2.7 eq) and phenyl octylamine (0.070 mL, 0.35 mmol, 1.3 eq) and the reaction was stirred overnight at rt. Additional 1,1′-carbonyldiimidazole (0.124 g, 0.76 mmol 2.8 eq) and phenyl octylamine (0.070 mL, 0.35 mmol, 1.3 eq) was added and stirring was continued overnight. The solids were then filtered off and washed with EtOAc. The filtrate was washed with saturated NaHCO3 solution, 0.1 N HCl and brine. It was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (20% EtOAc: Hexane+1% Formic acid) to afford the title compound (0.150 g, 37%) as a light yellow oil. 1H NMR (DMSO-d6 δ 8.20 (t, 1H); 7.81–7.70 (m, 8H); 7.61 (s, 2H); 7.25–7.12 (m, 5H); 4.87 (s, 2H); 3.19 (dd, 2H); 2.52 (t, 2H); 1.50 (m, 4H); 1.28 (m, 8H); IR (KBr) 3540, 3350, 2950, 2850, 1620, 1545, 1480, 1420, 1325, 1180, 1120, 1110, 1080 cm−1; mass spectrum [(+)APCI], m/z 613 (M+H)+; Anal. Calcd. for C35H34F6N2O: C, 68.62; H, 5.59; N, 4.57. Found: C, 67.66; H, 5.96; N, 4.33.

Provenance & Evidence