2-Chloropropionyl chloride → 5-(1-Chloroethyl)-3-(3-chlorophenyl)-1,2,4-oxadiazole

Participants

Reaction Conditions

Reaction Steps

1.80 g 3-chloro-N′-hydroxybenzenecarboximidamide and 3.7 mL DEA were dissolved under Ar in DCM (100 mL) and cooled on an ice/water bath, followed by addition of 2-chloropropanoyl chloride. After 1 h at r.t. the mixture was concentrated and the crude taken up in DMF (120 mL), followed by heating for at 120° C. for 2 h. The mixture was concentrated onto celite and purified via column chromatography (hep 100% to hep/EA=7/3) yielding the title compound (1.72 g, 67%). 1H NMR: 8.09 (t, 1 H), 7.93-8.02 (m, 1 H), 7.38-7.54 (m, 2 H), 5.22 (q, 1 H), 2.02 (d, 3 H)

Provenance & Evidence