Allyl bromide → 5-[4-(1,1-Dimethylethyl)phenyl]-4-(2-propenylthio)-1,2,3-thiadiazole

Participants

Reaction Steps

A solution of 1.45 g of 5-[4-(1,1-dimethylethyl)-phenyl-1,2,3-thiadiazole-4-thiol, potassium salt in 50 ml of ethanol was stirred overnight with 3.0 g of allyl bromide. The solvent was removed in vacuo, the residue taken up in ether, filtered and concentrated in vacuo. The residual oil was dissolved in a small amount of dichloromethane and purified on thick layer silica gel plates, eluting with the same solvent. The active fraction gave 1.225 g of the desired compound as a yellow oil. Proton nuclear magnetic resonance (δ[ppm], CDCl3) 90 MHz: 1.39 (s, 9H, t-butyl); 3.98 (bd, 2H, SCH2); 5.05 (bd, 1H, CH=); 5.20 (bd, 1H, =CH); 5.87 (m, 1H, CH2CH=); 7.55 (s, 4H, C6H4). Infrared absorption spectrum (neat): 1640(w); 1615(w); 1525(w); 1480(w); 1475(w); 1450(w); 1410(w); 1370(w); 1270(w); 930(s); 820(s).

Provenance & Evidence