Sodium Chloride → HCID 11321832, compound

Participants

Reaction Steps

A solution of Br2 (0.71 ml, 13.9 mmol, 1 equiv.) in DMF (5 ml) is added over 10 min to a solution of N-methoxycarbonyl-1,2-dihydropyridine 1 (1.92 g, 13 mmol, 1 equiv.) and of thiourea (3.95 g, 52 mmol, 4 equiv.) in DMF (15 ml)/CH3CN (5 ml) at ambient temperature and under argon. The reaction being complete from the end of the addition of the bromine, the reaction mixture is concentrated approximately twofold, poured onto ice-cold water (200 ml) and then filtered through a Buchner funnel. The filtrate is basified (5% Na2CO3) until a pH of greater than 10 is obtained and is then saturated with NaCl. After extracting with DCM, drying over MgSO4 and evaporating the solvent, the liquid obtained (10.8 g) is chromatographed on silica gel using DCM (sat. NH3) and then DCM (sat. NH3)/MeOH, 2%. The product 6 (Rf=0.39, DCM/MeOH(NH3), 98:2) is obtained in the form of a white solid (0.32 g, 11%).

Provenance & Evidence