Imidazole → HCID 57781089, compound

Participants

Reaction Conditions

Reaction Steps

A flask is charged with polymer-supported triphenylphosphine (1.48 mmol/g, 6.87 g, 10.17 mmol) and dichloromethane (70 mL). Bromine (1.58 g, 9.77 mmol) is added at r.t., followed with N,N-diethyl-3,4-difluoro-2-hydroxymethyl-benzamide (1.100 g, 4.070 mmol) in dichloromethane (15 mL). After 5 min, the mixture is filtered and the resin is washed several times with dichloromethane. The resulting filtrate is concentrated in vacuo to yield an oil. Imidazole (2.80 g, 40.70 mmol) is added, followed with acetonitrile (30 mL) and the mixture is heated to 70° C. After 5 min at 70° C., the mixture is allowed to cool down, diluted with ethyl acetate and extracted three times with 1M aqueous HCl. The combined aqueous phase is washed once with dichloromethane. The aqueous phase is then cooled to 0° C. and the pH is adjusted to 12 with cold 4M aqueous NaOH. The aqueous phase is then extracted with dichloromethane. The combined extraction fractions are dried over MgSO4 and filtered. The sample is concentrated in vacuo, taken up in ethyl acetate and washed with water (three times), and brine. The organic phase is dried over MgSO4, filtered and concentrated in vacuo to give N,N-diethyl-3,4-difluoro-2-imidazol-1-ylmethyl-benzamide as a yellow oil; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.95 (t, J=7.1 Hz, 3 H), 1.26 (t, J=7.1 Hz, 3 H), 2.82 (q, J=7.1 Hz, 2 H), 3.52 (q, J=7.1 Hz, 2 H), 5.25 (br. s., 2 H), 6.96 (s, 1 H), 6.98-7.03 (m, 1 H), 7.01 (s, 1 H), 7.16-7.25 (m, 1 H), 7.51 (s, 1 H).

Provenance & Evidence