The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Pyridine mercurials》. Authors are Hurd, Charles D.; Morrissey, Clarence J..The article about the compound:2-Chloro-5-pyridinesulfonyl chloridecas:6684-39-5,SMILESS:ClC1=NC=C(C=C1)[S](=O)(=O)Cl).Name: 2-Chloro-5-pyridinesulfonyl chloride. Through the article, more information about this compound (cas:6684-39-5) is conveyed.
The preparation and properties of di-3-pyridylmercury (I), bis(3-pyridylmercuri)ammonium chloride (II), 6-chloro-3-pyridylmercuric chloride (III), and 2-pyridylmercuric chloride (IV) are described. 3-Pyridylmercuric acetate (V) (75 g.) in 3 l. H2O at 80° treated dropwise with 13 g. NaCl in 50 cc. H2O gave 81% 3-pyridylmercuric chloride (VI), m. about 245°; it gave recrystallized from H2O (2 g./1 l.) needles, m. 265-8°. V in hot H2O treated with aqueous NaBr gave 3-pyridylmercuric bromide, m. 275° (decomposition). Similarly was obtained the corresponding iodide, yellow solid, m. 280° (decomposition). Br (10 g.) added during 3.5 h. with stirring to 20 g. VI and 6.6 g. NaBr in H2O at 50-60°, the mixture held 15 h. at 20°, treated with 5.7 g. HCl, and filtered from 16.4 g. residue, the filtrate basified and extracted with Et2O, and the residue (3.0 g.) from the extract redistilled yielded 1.6 g. 3-bromopyridine, b. 168-71.5°. VI (0.2 g.) refluxed 0.5 h. with 25 cc. 0.1N iodine containing 1 g. KI and 3 cc. CHCl3, and the mixture titrated with 0.1N Na2S2O3 indicated a quant. reaction. VI (10 g.), m. 245°, and 100 g. NH4OH stirred occasionally during 0.5 h. and filtered gave 5.1 g. solid filter residue of II, m. 168-80°, which liberated NH3 when boiled with dilute NaOH; the filtrate evaporated and the solid residue (4.8 g.) leached with H2O left unchanged VI, m. 240°. Na2S2O3 (50 g.) in 50 cc. H2O treated with 10 g. V, and the solution allowed to stand 0.5 h. gave 4.5 g. I, white solid, m. 225-6°. II (1 g.) mixed with 10 saturated aqueous Na2S2O3, and the precipitate recrystallized from EtOH gave I, m. 255°, which recrystallized from EtOH gave crystals, m. 239°. I in EtOH mixed with alc. HgCl2 gave VI, m. 240-5°. I in EtOH treated with alc. gave the di-HCl salt, white crystals, m. 222° (decomposition). Similarly was prepared the dipicrate, yellow crystals, m. 255° (decomposition). I.2HCl heated to 200° evolved pyridine. I dipicrate treated with alc. KOH gave I, m. 237-8°. The urethane of 3-aminopyridine (VII) acidified with HCl and heated to 100° until the effervescence ceased, the H2O evaporated, and the residue dissolved in hot C6H6 and precipitated with 2 volumes ligroine gave the amine, m. 62°, in 40% yield. VII (1.88 g.) was diazotized in 6 cc. cold. concentrated HCl with 1.4 g. NaNO2 in 6 cc. H2O and then 5.4 g. HgCl2 in 6 cc. HCl added to yield 6.2 g. diazonium salt-HgCl2 double salt (VIII). VIII (5 g.) mixed with cooling with 5 g. Cu in 30 cc. Me2CO, the mixture treated with 30 cc. NH4OH, allowed to stand 15 h., diluted with an equal volume H2O, and filtered, the filter residue extracted in a Soxhlet apparatus 1 h. with Me2CO, the extract evaporated, and the residue (0.8 g.) crystallized from a little EtOH gave I, m. 232°. VI (10 g.) added to 50 cc. cold NH4OH, the mixture filtered after 0.5 h., the filtrate treated with 10 g. Cu powder, and filtered after several days, the filtrate evaporated to dryness, and the residue recrystallized from EtOH gave a small amount of I, m. 227-34°. 2-Pyridinethiol (22 g.) (from 2-bromopyridine and thiourea), 300 cc. HCl, and 70 cc. ice water treated at 0-5° with excess gaseous Cl, the mixture poured into 800 cc. ice water, and a part of the precipitate recrystallized by dissolving in (CH2Cl)2 at 40° and cooling to -5° gave an unidentified substance, white needles, m. 210° (from Me2CO); the remainder of the solid suspended in 200 cc. cold H2O, mixed with 40 g. Zn dust, heated 20 min. to boiling, made alk. with aqueous Na2CO3, and filtered, the filtrate neutralized, heated with 25 g. HgCl2 to boiling, refluxed 2 h., and filtered, and the filtrate neutralized with HCl yielded IV, white solid, m. 275° (from MeOH). 2-Chloro-5-pyridinesulfonyl chloride (25 g.), m. 51°, treated with vigorous stirring with 23 g. Zn dust, the mixture refluxed 0.5 h., made alk. with Na2CO3 and filtered, the filter residue washed with hot aqueous Na2CO3, the combined filtrates neutralized, treated with 32 g. HgCl2, refluxed 2 h., and filtered, and the filter residue washed with H2O and dried gave 4.5 g. solid, m. 130°, which heated twice with 10% aqueous NaOH at 80°, filtered hot, and washed with H2O yielded 1.5 g. III, m. 263°.
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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis