Potassium Carbonate → HCID 58930424, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-6-methoxybenzothiazole (1.00 g, 5.03 mmol) in DMF (10 mL) was added methyl 4-aminobenzoate (760 mg, 5.03 mmol) followed by addition of powdered K2CO3 (1.81 g, 15.09 mmol). The mixture was stirred at 90° C. for 16 h and at 120° C. for 24 h and then at 140° C. for 3 days. It was allowed to cool down to rt and NaH (60% in mineral oil, 201 mg, 5.03 mmol) was added. The mixture was stirred at rt for 16 h and quenched with H2O. The solvent was removed in vacuo at 80° C. and the residue was partitioned between H2O and EtOAc. The organic layer was washed with HCl 1N, saturated NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography using EtOAc/Hex and increasing polarity from 20:80 to 50:50 throughout elution, affording the title compound 161 (150 mg, 9% yield). m/z: 315.2 (MH+)

Provenance & Evidence