Ammonium Chloride → HCID 57546216, compound

Participants

Reaction Conditions

Reaction Steps

1-(Cyclopropylmethyl)-6-(trifluoromethyl)-1H-benzo[d]imidazole-4-carbaldehyde (0.323 g, 1.2 mmol) was dissolved in tetrahydrofuran (6 mL), cooled down to 0° C. and to it was added methylmagnesium bromide (1.0 M in dibutyl ether, 2.2 mL, 2.2 mmol) dropwise. After 1.5 h, saturated aqueous ammonium chloride was added and the mixture was extracted with ethyl acetate (3×30 mL). The organic layer was washed with water (20 mL), brine (20 mL) and dried (Na2SO4). The crude product obtained after evaporation of solvent was purified by flash chromatography on silica gel (2% MeOH/CH2Cl2) affording 286 mg (84%) of product as light yellow oil. 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 8.11 (s, 1 H), 7.62 (s, 1 H), 7.46 (s, 1 H), 5.38-5.49 (m, 1 H), 4.16 (d, J=6.1 Hz, 1 H), 4.06 (d, J=7.0 Hz, 2 H), 1.70 (d, J=6.7 Hz, 3 H), 1.29-1.40 (m, 1 H), 0.69-0.80 (m, 2 H), 0.45 (q, J=5.2 Hz, 2 H). 308.17 (MNa)+.

Provenance & Evidence