Tert-Butyl nitrite → 1-Chloro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

Participants

Reaction Conditions

Reaction Steps

2-Amino-N-(4-chloro-quinolin-8-yl)-benzenesulfonamide (Intermediate 275) (1.3 g, 3.89 mmol) was dissolved in AcOH (13 ml) and the mixture was stirred at 0° C. for 5 min. The solution was cooled to −10° C. and t-butyl nitrite (0.7 ml, 5.83 mmol) was added dropwise and the mixture was stirred at room temperature 30 min. The mixture was quenched with sat. NaHCO3 solution and the aqueous phase was extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (400 mg, 33%) after the purification by column chromatography with DCM/MeOH (90:10) as the eluent.

Provenance & Evidence