Cyanogen Bromide → HCID 10583156, compound

Participants

Reaction Conditions

Reaction Steps

A solution of cyanogen bromide (1.42 g, 13.4 mmol) in anhydrous diethyl ether (8 mL) was added slowly to a stirred solution of 3-(methylthio)aniline (2.72 mL, 21.4 mmol) in anhydrous diethyl ether at 4° C. After the addition, the reaction mixture was stirred at 24° C. for 12 hours and became a brown solution with a white precipitate. The precipitate was filtered off; the filtrate was washed with aqueous HCl (1 M, 3×15 mL) in ether and the organic layer extracted with brine (10 mL). Then the ether solution was dried over MgSO4, filtered, and concentrated in vacuo to yield a thick liquid. The crude product was further purified by column chromatography (SiO2, a gradient of hexanes/CH2Cl2/EtOAc) to afford 3-(methylthio)phenyl cyanamide (0.7 g, 49% yield) as a white solid: m.p. 64-65° C.;

Provenance & Evidence