Water → HCID 53959327, compound

Participants

Reaction Steps

Part C. A solution of the alcohol prepared above (5.96 g, 13.8 mmol), diisopropylethylamine (2.90 mL, 16.6 mmol) and toluenesulfonyl chloride (2.89 g, 15.2 mmol) in tetrahydrofuran (30 mL) was heated to reflux for 18 hours. The mixture was cooled, and poured into water (150 mL). This was extracted with methylene chloride (2×150 mL), and the extracts were combined, dried over magnesium sulfate and evaporated. The residual oil was separated by flash chromatography (3:7 ethyl acetate-hexane)to afford the product, 4,5-bis (4-methoxyphenyl)-2-[3-(chloro-methyl)benzyl]thio-1H-imidazole, as a foam upon vacuum pumping (2.24 g, 4.96 mmol, 36%). 1H NMR (CDCl3): 8.94 (1H, br s); 7.70-7.09 (8H, m); 6.84 (4H, d, J=8.8 Hz); 4.51 (2H, s); 4.19 (2H, s); 3.81 (6H, s).

Provenance & Evidence