Cyanogen Bromide → HCID 10583156, compound

To a cooled solution (0° C.) of 3-Methylthio-aniline (1.850 g, 13.30 mmol) in anhydrous diethylether (10 ml) was added a diethylether solution (10 ml) of cyanogen bromide (0.704 g, 6.65 mmol). CAUTION: Cyanogen bromide is highly toxic. The resulting solution was allowed to stir at room temperature over night. The resulting mixture was filtered to remove the precipitate and the diethylether filtrate was washed with 1M HCl (20 ml) and brine (20 ml) before the solvent was removed under vacuum to yield an oily yellow residue. Purification of the crude product by column chromatography on silica gel using 95:5 dichloromethane/ethyl acetate afforded (3-methylthio-phenyl)-cyanamide as a near colourless oil which crystallised on standing (0.570 g, 52%).

1. filtrationThe resulting mixture was filtered
2. customto remove the precipitate
3. washthe diethylether filtrate was washed with 1M HCl (20 ml) and brine (20 ml) before the solvent
4. customwas removed under vacuum
5. customto yield an oily yellow residue
6. customPurification of the crude product by column chromatography on silica gel using 95:5 dichloromethane/ethyl acetate

ORD record

ord-4597e616adce44c99f3d32dea105ef63

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08058311B2