Polyhalogeno-aromatic compounds. Part XXVIII. Derivatives of polyhalogenopyridine-4-thiols
Abstract
The tetrachloropyridine-4-sulphonamides (1)–(3) were prepared from tetrachloropyridine-4-sulphonyl chloride and allylamine, n-butylamine, or ethanolamine at low temperatures. Tetrachloropyridine-4-(N-2-hydroxyethyl)sulphonamide (3) can undergo a double Smiles-type rearrangement (Scheme 1) on treatment with base at room temperature to give N-(tetrachloro-4-pyridyl)ethanolamine (4). Some reactions of 3,5-dichloro-2,6-difluoro-(7) and 2,3,5-trichloro-6-fluoro-pyridine-4-thiol (8) are reported.