1H-1,2,4-Triazole → 1-[2-(4-Chlorophenyl)prop-2-en-1-yl]-1H-1,2,4-triazole

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride/oil (28 g, 0.7 mol @ 60%) in 800 ml of DMF, add in portions 1,2,4-triazole (50 g, 0.72 mol) at -10° to 0° C. Stir at 0.5° C. for 1 hour until soultion is clear brown. Add rapidly at -5° to 5° C. p-chloro-α-bromomethyl styrene (200 g, 0.86 mol total bromide, 0.56 mol allyl @ 65%). Stir and warm to room temperature over 2 hours. Evaporate off the DMF. Add saturated NaCl and extract the product with 2×300 ml of ethyl acetate. Dry the combined extracts over MgSO4 and filter. Evaporate the ethyl acetate and chromatograph the resultant oil on 2 Waters prep. 500 cartridges using ethyl acetate:hexane (1:1) as the eluent to obtain p-chloro-α-1H-1,2,4-triazolylmethyl styrene: 'HNMR (90 mHz, CDCl3) 8.06 (1 H, S), 7.93 (1H, S), 7.3 (H H, S), 5.59 (1H, S), 5.16 (3H, br S).

Provenance & Evidence