Sodium Sulfate → HCID 19809062, compound

Participants

Reaction Steps

To a solution of lithium aluminium hydride (1N in tetrahydrofuran, 2 mL) in dry tetrahydrofuran (30 mL), a solution of N-[5-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-ylthio]pentyl]-2,4-difluoro-N-heptylbenzeneacetamide (0.70 g, 0.00107 mol) in dry tetrahydrofuran (15 mL) was added slowly. The reaction mixture was heated to reflux for 5 hours and was then allowed to cool to ambient temperature. The reaction mixture was poured into a mixture of 10% aqueous sodium sulfate (150 mL) and ice (150 mL). The resultant emulsion was filtered through Celite® and the filtrate was extracted with ethyl acetate (3×100 mL). The organic layer was washed with water, brine, dried over magnesium sulfate and concentrated in vacuo to give a crude oil. The product was purified by flash chromatography on silica gel (100 mL) eluting methanol: methylene chloride (5:95 v:v) to give the title compound as a viscous colorless oil (0.46 g, 0.000723 mol). 1H NMR (CDCl3) δ9.2-9.15(bs,1H), 7.56-7.25(m,4H), 7.11(m,1H), 6.94-6.70(m,6H), 3.81(m,6H), 3.07(t,2H), 2.74-2.58(m,4H), 2.43(m,4H), 1.71(m,2H), 1.53-1.20(m,14H), 0.91(t,3H).

Provenance & Evidence