Pyridine → HCID 10593784, compound

Participants

Reaction Steps

To 2-amino-5-(methoxycarbonyl)benzaldehyde trimethylene mercaptal (Gassman, P. G.; Drews, H. R. J. Am. Chem. Soc. 1978, 100, 7600-7610) (5.0 g, 0.019 mol) in dichloromethane (90 mL) was added pyridine (4.51 mL, 0.055 mol). Methanesulfonyl chloride (4.31 mL, 0.055 mol) was then added over a five-minute period and the reaction mixture heated at reflux overnight. Thin-layer chromatography analysis (SiO2, EtOAc:hexane 1:1) showed the disappearance of the starting material along with the appearance of a new lower-running spot (Rf =0.56) indicating the reaction was complete. Upon cooling, the reaction was washed thoroughly with 10% acetic acid followed by water. The organic layer was dried (Na2SO4), filtered, and concentrated. The crude residue was placed on a SiO2 column and eluted with 1:1 EtOAc:hexane. Fractions containing the desired product were combined and concentrated to yield 5.0 g (77%) of 2-(methanesulfonylamino)-5-(methoxycarbonyl)benzaldehyde trimethylene mercaptal as a yellow solid. An analytical sample, mp 168°-168.5° C., was recrystallized from ethanol.

Provenance & Evidence