The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Some reactions of 2,4-dimethylmagnesylpyrrole》. Authors are Ingraffia, F..The article about the compound:Ethyl 3,5-Dimethyl-2-pyrrolecarboxylatecas:2199-44-2,SMILESS:O=C(C1=C(C)C=C(C)N1)OCC).Safety of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. Through the article, more information about this compound (cas:2199-44-2) is conveyed.
Because of the anomalous behavior of magnesylpyrrole with SOCl2 (I) and CS2 (cf. Oddo and Mingoia, C. A. 21, 1458), it was decided to study their action as well as that of ClCO2Et (II) on a little studied derivative of pyrrole, viz., 2,4-dimethylpyrrole (III) in the form of its magnesyl derivative (IV), and on magnesylpyrroles with neg. radicals (to stabilize the ring). IV and II in anhydrous Et2O, heated, and decomposed with ice, yield Et 2,4-dimethyl-5-pyrrolecarboxylate, HN.CMe:CH.CMe:CCO2Et (V), slightly yellow, m. 124°. I in Et2O added to ice-cold IV (2 mols.) in Et2O, after standing decomposed with ice, neutralized with NaHCO3 and purified with difficulty (Et2O, petr. ether, Me2CO and C6H6), yields 3,5,3′,5′-tetramethylpyrro-(2,2′)-sulfone, (HN.CMe:CH.CMe:C)2SO2, dark violet, decomposes around 95° stable toward hot alk. hydroxides, is not reduced by Zn and AcOH, is decomposed with evolution of H2S by Sn in hot HCl. Ag derivative, probably an α’-derivative IV and CS2 in Et2O heated, decomposed with ice, acidified with H2O4, the Et2O-soluble product treated with aqueous NaOH, and acidified when ice-cold, precipitates 2,4-dimethyl-5-dithiopyrrolecarboxylic acid, HN.CMe:CH.CMe:CC(:S)SH (VI), also obtained directly but very impure by drying the Et2O-soluble portion (loc. cit.). It is unstable and immediately oxidizes to 2,4-dimethylthiopyrrole disulfide, [HN.CMe:CH.CMe:CC(:S)S-]2, red, m. 156°. With neutral Pb(OAc)2, the aqueous Na salt (VII) of VI precipitates the Pb salt, [HN.CMe:CH.CMe:CC(:S)S]2Pb, yellow. In darkness, aqueous VI and AgNO3 precipitate the Ag salt, HN.CMe:CH.CMe:CC(:S)SAg, brick-red. No Zn salt is precipitated from aqueous VII and Zn(OAc)2. It was then to be determined whether with a compound containing a neg. CO2Et group, e. g., V, the reaction with EtMgBr is normal, and if so to determine the behavior of the new metal derivative in comparison with III. Actually V and EtMgBr in anhydrous Et2O evolve C2H6 and form the magnesyl derivative (VIII), BrMgN.CMe:CH.CMe:CCO2Et or HN.CMe:C(MgBr).CMe:CCO2Et, yellowish oil. Heated with CS2 or with AcCl in anhydrous Et2O, VIII remains unaltered. This incapacity to react probably depends upon the assumption of the enolic form, N:CMe.CH:CMe.C:C(OMgBr)OEt, as was found with alkyl pyrryl ketones by Oddo (C. A. 19, 2492; Gazz. chim. ital. 40, ii, 15(1910); cf. C. A. 4, 2460).
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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com