Benzyl Bromide → HCID 22100950, compound

Participants

Reaction Steps

4-(5-Trifluoromethylbenzothiazol-2-yl)pyridine (10 g, 0.04 mol) was reacted with benzyl bromide (6.4 ml, 0.06 mol) followed by sodium borohydride (1.76 g, 0.052 mol) as exemplified in Example 7 step 2. The crude product was purified by flash chromatography eluting with 15% ethyl acetate in petroleum ether to give a yellow solid. Recrystallisation from ethyl acetate afforded the title compound as a pale yellow solid (7 g, 47%); mp. 124°-125° C.; (Found: C, 63.85; H, 4.48; N, 7.48. C20 H17F3N2S requires C, 64.16; H, 4.58; N, 7.48%). δH (CDCl3), 2.75 (2H, m, NCH2CH2), 2.81 (2H, m, NCH2CH2), 3.24 (2H, m, NCH2CH2), 3.67 (2H, s, NCH2Ar), 6.71 (1H, m, NCH2CH), 7.28 (5H, m, ArH), 7.55 (1H, d of d, J 8.4Hz, J 1.4Hz, ArH), 7.89 (1H, d, J 8.4Hz, ArH), 8.23 (1H, s, ArH); m/z (ES+) 375 (M+1)+.

Provenance & Evidence