Phenylacetonitrile → HCID 178510757, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of Example 227C (0.96 g, 4.48 mmol) in DMF (20 mL) at −35° C. was added benzyl cyanide (1.55 mL, 13.4 mmol) and then NaH (0.57 g of 95% NaH, 22.4 mmol). The resulting dark red mixture was stirred 15 min while being slowly warmed to ˜−20° C. At this time most of the bubbling had stopped and the reaction mixture was then quickly warmed to room temperature and then to 100° C. overnight. The reaction mixture was cooled to room temperature and saturated aqueous NH4Cl was added. The mixture was extracted with EtOAc and the organic extracts washed twice with H2O and once with brine. Silica gel was added and the volatiles removed on a rotary evaporator. Flash chromatography (60-80-100% EtOAc-3% MeOH/EtOAc) gave 1.14 g (82%) of as an orange solid. Rf=0.40 (5% MeOH/EtOAc); MS m/z 312 (M+H)+; 1H NMR (300 MHz, DMSO-D6) δ ppm 6.17 (s, 1 H) 7.40 (m, 4 H) 7.52 (m, 2 H) 8.00 (m, 2 H) 8.70 (m, 2 H) 8.74 (d, J=8.48 Hz, 1 H) 14.36 (s, 1 H); Anal Calcd for C19H13N5: C, 73.30; H, 4.21; N, 22.49. Found: C, 73.09; H, 4.10; N, 22.58.

Provenance & Evidence