Thionyl Chloride → HCID 21886113, compound

Participants

Reaction Steps

Thionyl chloride (5.6 mL) was added over 1 min to a 0° C. solution of 3-iodo-4-methyl benzoic acid (5 g, 19.1 mmol) in THF (30 mL). The solution was stirred for 24 h at rt and the volatile components were removed in vacuo. A portion of the crude acid chloride (1 g, 3.57 mmol) was dissolved in DCM (10 mL) and was cooled to 0° C. Diisopropylethylamine (0.78 mL, 4.46 mmol) was added followed by 3-morpholin-4-yl-propylamine (0.52 mL, 3.56 mmol) and the reaction was stirred for 1 h at rt. EtOAc (80 mL) and aq. NH4Cl (20 mL) was added and the layers were separated. The organic layer was washed with aq NH4Cl (2×10 mL), NaOH (1N, 3×20 mL), water (20 mL), brine (50 mL) and was dried over sodium sulfate. Concentration of the solution and SiO2 flash column chromatography of the residue (0–10% MeOH in DCM) yielded the product (695 mg, 50%) as a yellow glass.

Provenance & Evidence