Chloroform → HCID 19815311, compound

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Reaction Steps

Thionyl chloride (3.60 mL, 49 mmol, 5 eq) was slowly dripped into a solution of 2-butyl-4-chloro-1-(4-cyanobenzyl)-5-hydroxymethylimidazole (3.0 g, 9.9 mmol, 1 eq) in a minimum of CHCl3. The mixture was stirred for 2 hours at room temperature after which the solvent was removed in vacuo and the residue suspended in toluene (200 mL). The toluene was removed on the rotary evaporator and this procedure was repeated again to remove all traces of thionyl chloride. The chloride was then dissolved in DMSO (minimum to dissolve) and added to a solution of sodium cyanide (2.90 g, 59 mmol, 6 eq) in DMSO (200 ml). The solution was stirred overnight under N2 at room temperature after which 500 mL H2O was added and the aqueous layer was extracted three times with 300 mL of ethyl acetate. The organic layers were dried and concentrated and the residue flash chromatographed in 4:1 hexane/ethyl acetate over silica gel to give 1.62 g of a light yellow solid; m.p. 109.5°-113.0° NMR (200 MHz, CDCl3) δ 7.70 (d, 2H, J=10Hz); 7.12 (d, 2H, J=10Hz); 3.51 (s, 2H); 2.60 (t, 2H, J=7Hz); 1.70 (m, 2H); 1.40 (m, 2H); 0.90 (t, 3H, J=7Hz). Mass spectrum shows M+ =312/314. Mass Calcd. for C17H17ClN4 : 312.1139, Found 312.1126.

Provenance & Evidence