Dimethylformamide → HCID 70654232, compound

Participants

Reaction Steps

To a solution of 2,3-bis(4-methoxyphenyl)quinoxaline-6-sulfonic acid (137.2 mg, 0.33 mmol, 1.00 equiv) in thionyl chloride (12 mL) was added N,N-dimethylformamide (2 mL) dropwise with stifling. The mixture was stirred at reflux for 3 hr in an oil bath. The resulting mixture was concentrated in vacuo. The residue was dissolved in acetonitrile (10 mL) and added to a solution of ammonia (2 g) in acetonitrile (10 mL) dropwise at 0° C. The resulting mixture was stirred overnight at room temperature, then concentrated in vacuo. The crude product (100 mg) was purified by Prep-HPLC with the following conditions (AGILENT Pre-HPLC (UV-Directed)): Column, SunFire Prep C18, 5 um, 19*100 mm; mobile phase, water with 0.05% TFA and CH3CN (10% CH3CN up to 65% in 2.8 min, hold 65% in 2.5 min, up to 100% in 0.1 min, hold 100% in 0.6 min, down to 10% in 0.1 min); Detector, UV 254 nm. This resulted in 16 mg (12%) of 2,3-bis(4-methoxyphenyl)quinoxaline-6-sulfonamide as a light yellow solid.

Provenance & Evidence