The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Antituberculous compounds. II. 2-(Benzylidenehydrazino)benzothiazoles》. Authors are Katz, Leon.The article about the compound:2-Chloro-6-nitrobenzo[d]thiazolecas:2407-11-6,SMILESS:O=[N+](C1=CC=C2N=C(Cl)SC2=C1)[O-]).Quality Control of 2-Chloro-6-nitrobenzo[d]thiazole. Through the article, more information about this compound (cas:2407-11-6) is conveyed.
cf. C.A. 46, 933g. 2-Chlorobenzothiazole (I) (170 g.) added during 1 hr. to 300 g. gently refluxing 85% N2H4.H2O (5.1 moles), and the slurry refluxed 15 min., cooled, and filtered yielded 150.6 g. 2-hydrazinobenzothiazole (II), m. 197-9° (all m.ps. uncorrected). p-H2NC6H4CHO (0.075 mole) and 30 g. AcOH heated to 100°, 45 g. succinic anhydride added, the mixture held 3.5 hrs. at 95-100°, diluted with 150 cc. AcOH, let cool overnight, filtered, the dried, powd. cake in 300 cc. water containing 50 cc. concentrated NH4OH stirred 1 hr., 20 g. Supercel added, the mixture filtered, the filtrate acidified with 6 N HCl, and the precipitate filtered off and washed with 500 cc. water yielded 12.5 g. p-(succinylamino)benzaldehyde, HO2CCH2CH2CONHC6H4CHO (III), pale yellow cubes from HCONH2, m. 231-2.5°. p-AcNHC6H4CHO (13.5 g.) added to 150 cc. boiling AcOH and 16.9 g. II, and the slurry stirred 10 min., cooled, filtered, and washed with 300 cc. MeOH yielded 19.5 g. white solid (3.4 g. more from the filtrate), m. 291-3° (from AcOH) (also given as 294-6° from HCONH2, compound 4 below). The preceding method was used for compounds 1-7 below. I (101 g.) added dropwise during 30 min. to 800 g. concentrated H2SO4 at 10-17°, 66 g. powd. KNO3 added portionwise during 1 hr. to the solution cooled to 12° (temperature not to exceed 18°), the solution stirred 15 min., warmed to 25° 30 min., and, after the temperature had risen to 40°, poured into 4 l. ice and water, 6 l. water added, and the solid filtered off yielded 122 g. 2-chloro-6-nitrobenzothiazole (IV), m. 190-1° (from EtOH). N2H4.H2O (300 g.), preheated to 80°, added to 2 l. refluxing EtOH containing 57.0 g. IV, and the mixture stirred 15 min., filtered hot, and washed with 500 cc. EtOH yielded 48.2 g. 6-nitro-2-hydrazinobenzothiazole (V), m. 264-6° (decomposition) (from HCONMe2). Compounds 8-14 below were prepared by the following method: p-HOC6H4CHO (15.0 g.) added to 21.0 g. V and 150 cc. dioxane in 500 cc. boiling AcOH, and the solution held 15 min. at 105-7°, cooled to room temperature overnight, filtered, and washed with 250 cc. MeOH yielded 18.1 g. compound 8; the filtrate, diluted to 1.33 l. with water, yielded 4.9 g. more. III (8.8 g.) in 50 cc. boiling water containing 3 cc. concentrated NH4OH added to 350 cc. boiling AcOH containing 11.0 g. V and 10 cc. HCONH2, and the mixture cooled to room temperature, diluted with 300 cc. MeOH, and filtered yielded 14.1 g. compound 13, m. 319-21°. IV (21.0 g.) added portionwise during 1 hr. to 150 cc. EtOH, 10 g. AcOH, 250 cc. water, and 50 g. 100-mesh Fe which had been heated to 80-5° 30 min., the mixture held at 80° 1 hr., 200 cc. EtOH and 10 g. Darco G-60 added, the mixture refluxed 15 min., filtered hot into 250 cc. water, and the filtrate chilled yielded 13.8 g. 6-amino-2-chlorobenzothiazole (VI), m. 155-7°. AcCl (10.8 g.) added dropwise during 20 min. to 18.4 g. VI and 70 cc. pyridine at 10°, and the mixture stirred 30 min. at 0-10°, poured into 800 cc. water, and filtered yielded 21.6 g. 6-Ac derivative (VII), fine white needles from the min. amount of EtOH added to 40 volumes hot water, m. 131-2°. VII (42.5 g.) added quickly to 150 g. boiling N2H4.H2O, the slurry diluted with 125 cc. hot water, boiled 5 min., 150 g. ice added, and the mixture filtered yielded 38.3 g. 6-acetamido-2-hydrazinobenzothiazole (VIII), m. 233-5° (from aqueous MeOH). Compounds 15-20 were prepared by the following method: VIII (3.0 g.) in 100 cc. boiling 25% AcOH treated with 3.0 g. p-HOC6H4CHO, and the mixture stirred 10 min., cooled, and filtered yielded 3.4 g. compound 15, m. 274-7°. VI (10 g.) and 50 g. N2H4.H2O boiled 5 min., cooled to 20°, and filtered yielded 8.6 g. 6-amino-2-hydrazinobenzothiazole, m. 209.5-11° (from iso-PrOH). Pyridine (20 cc.), 1.3 g. VI, and 2.0 g. PhSO2Cl heated to boiling, and the solution cooled and poured into 150 cc. water yielded 2.1 g. 2-chloro-6-(phenylsulfonamido)benzothiazole (IX), m. 176-7.5° (from aqueous EtOH). IX (2.1 g.) and 20 g. N2H4.H2O boiled 5 min., cooled, and neutralized with 6 N H2SO4 yielded 1.7 g. 2-hydrazino-6-(phenylsulfonamido)benzothiazole, pale yellow crystals from PhMe-EtOH, m. 214-16°. For the 2-(benzylidinehydrazino)benzothiazoles (X), the compound number, R, R1, yield (%), m.p. (uncorrected), and recrystallization solvent are: 1, H, OH, 80,253-4.5°, AcOH; 2, H, Ac, 70, 194-5°, iso-PrOH; 3, H, OCH2CO2H, 81, 254-7° dioxane; 4, H, NHAc, 89, 294-6°, HCONH2; 5, H, NMe2, 77, 243-4.5° iso-PrOH; 6, H, NHCOCH2CH2CO2H, 91, 255-7°, AcOH; 7, H, CO2H, 86, 319-20°, HCONH2; 8, NO2, OH, 73, 318-19°, HCONH2; 9, NO2, OMe, 72, 299-300° AcOH; 10, NO2, OCH2CO2H, 68, 280-1.5° HCONH2; 11, NO2, NHAc, 70, 312-13° HCONMe2; 12, NO2, NMe2, 77, 263-5° AcOH; 13, NO2, NHCOCH2CH2CO2H, 81, 326-8°, HCONH2; 14, NO2, CO2H, 69, 331-2° AcOHHCONH2 (3:2); 15, NHAc, OH, 77, 279-81°, 50% aqueous HCONH2; 16, NHAc, OMe, 93, 262-3° HCONH2; 17, NHAc, OCH2CO2H, 84, 296-7° HCONH2; 18, NHAc, NHAc, 89, 292-3°, HCONH2; 19, NHAc, NMe2, 91, 286-7° HCONH2; 20, NHAc, CO2H, 86, 326-7°, AcOH. Compounds 3 and 5 were the most active.
There is still a lot of research devoted to this compound(SMILES:O=[N+](C1=CC=C2N=C(Cl)SC2=C1)[O-])Quality Control of 2-Chloro-6-nitrobenzo[d]thiazole, and with the development of science, more effects of this compound(2407-11-6) can be discovered.
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Highly efficient and robust molecular ruthenium catalysts for water oxidation,
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