Toluene → HCID 58217128, compound

Participants

Reaction Steps

Thionyl chloride (1 mL, 13.7 mmol) was added to a suspension of the acid (315 mg, 2 mmol) in toluene (5 mL). A drop of DMF was then added and after stirring at RT for 10 min. the mixture was heated at reflux for 1 h. The reaction was cooled to RT and toluene and excess thionyl chloride were removed under reduced pressure. Toluene (1 mL) was then added to the residue and this was removed under reduced pressure. This process was repeated, and then CH2Cl2 (10 mL) was added and the resulting solution cooled to t-Butylamine (0.45 mL, 4.3 mmol) and triethylamine (1.1 mL, 8.0 mmol) were than added and the solution stirred at RT overnight. The solution was diluted with CH2Cl2 (10 mL) and H2O (10 mL) and the organic layer collected and washed with aq. Na2CO3 and then dried (Na2SO4). The solvent was removed in vacuo and flash chromatography of the residue using CH2Cl2-MeOH (95:5) separated the pure product as an oil (290 mg, 68%).

Provenance & Evidence