{"id":11127,"date":"2022-11-21T04:59:04","date_gmt":"2022-11-20T20:59:04","guid":{"rendered":"https:\/\/www.pyrazoles-derivatives.com\/?p=11127"},"modified":"2022-11-21T04:59:04","modified_gmt":"2022-11-20T20:59:04","slug":"beyer-hanss-team-published-research-in-chemische-berichte-in-89-cas-23286-70-6","status":"publish","type":"post","link":"https:\/\/www.pyrazoles-derivatives.com\/?p=11127","title":{"rendered":"Beyer, Hans’s team published research in Chemische Berichte in 89 | CAS: 23286-70-6"},"content":{"rendered":"

Beyer, Hans published the artcileThiazoles. XXVIII. 2,2′-Dithiazolylamine and its nitration products<\/i><\/b>, Category: pyrazoles-derivatives<\/a>, the publication is Chemische Berichte (1956), 1602-8, database is CAplus.<\/p>\n

cf. C.A. 51, 2813c. 4,4′-Di- and 4,4′,5,5′-tetrasubstituted 2,2′-dithiazolylamines have been prepared Heating 4.5 g. dithiobiuret (I) and 11 g. CH2<\/sub>ClCHClOEt in 80 cc. 60% EtOH 1 hr. on a water bath, adding 30 cc. 5% HCl, decomposing the precipitated HCl salt with NaOAc, and concentrating the solution to 10 cc. yield 64% 2,2′-dithiazolylamine (II), yellow leaflets, m. 215\u00b0, which is also obtained in 75% yield when 6.8 g. I and 7.8 g. CH2<\/sub>ClCHO is heated 1 hr. on a water bath and the precipitated II.HCl is treated with NaOAc (HCl salt, needles, m. 214\u00b0; N-Ac derivative, small rods, m. 121-2\u00b0). Heating an intimate mixture of 11.4 g. 2-amino-4-methylthiazole (III) and 15 g. III.HCl 0.5 hr. at 200\u00b0, extracting the powd. melt with boiling H2<\/sub>O, and recrystallizing the residue from 2N HCL give 30% 4,4′-dimethyl-2,2′-dithiazolylamine (IV).HCl, yellow needles, m. 276-8\u00b0 (decomposition), which, with NaOAc, yields IV, needles, m. 153-4\u00b0, also obtained in 70% yield on heating 5.4 g. I with 11.1 g. AcCH2<\/sub>Cl in 50 cc. EtOH 2 hrs. on a water bath. Heating a mixture of 17.6 g. 2-amino-4-phenylthiazole (V) and 21.5 g. V.HBr 1 hr. at 200\u00b0, extracting the powd. melt with hot H2<\/sub>O and C6<\/sub>H6<\/sub>, and recrystallizing the residue from Me2<\/sub>CO yield 85% 4,4′-diphenyl-2,2′-dithiazolylamine (VI), yellow rhombs, m. 219-21\u00b0, also obtained in 93% yield on mixing 2.7 g. I and 8 g. PhCOCH2<\/sub>Cl, each dissolved in 25 cc. EtOH (N-Ac derivative of VI, needles or leaflets, m. 138\u00b0; N-Bz derivative, needles, m. 165-7\u00b0). Treating 3.3 g. VI in 150 cc. AcOH with solid NaNO2<\/sub> in small portions with cooling gives 72% 4,4′-diphenyl-2,2′-dithiazolylnitrosamine, red-brown cubes, m. 228-9\u00b0 (decomposition), crystallizing from C5<\/sub>H5<\/sub>N with 1 mol. C5<\/sub>H5<\/sub>N, red rods, losing its C5<\/sub>H5<\/sub>N on heating at 200\u00b0. Treating 5.5 g. 2-amino-4,5-dimethylthiazole-HCl with 0.66 g. solid NaOH 15 min. at 220\u00b0 yields 53% 4,4′,5,5′-tetramethyl-2,2′-dithiazolylamine, rhombs, m. 215-16\u00b0, which is also obtained in 78% yield when 1.3 g. I and 2.8 g. AcCHClMe is refluxed 0.5 hr. in 10 cc. MeOH. Fusing 29.3 g. 2-amino-4,5-diphenylthiazole (VII).HCl (or HBr) and 25.7 g. VII 0.5 hr. at 220\u00b0 and triturating the melt with hot H2<\/sub>O give 40% (or 70%) 4,4′,5,5′-tetraphenyl-2,2′-dithiazolylamine, rhombic leaflets, m. 208-9\u00b0, which is also obtained in 60% yield when 1.3 g. I and 3.2 g. desyl chloride is refluxed 1 hr. in 20 cc. EtOH (Ac derivative, platelets, m. 213-15\u00b0). Refluxing 1.7 g. 4-methyl-2-thiazolylthiourea and 2 g. PhCOCH2<\/sub>Br in 50 cc. EtOH 1 hr. yields 90% 4-methyl-4′-phenyl-2,2′-dithiazolylamine, needles, m. 245\u00b0. Heating 2.6 g. I and 9.6 g. m-O2<\/sub>NC6<\/sub>H4<\/sub>COCH2<\/sub>Br in 100 cc. EtOH 1 hr. on a water bath gives 85% 4,4′-bis(m-nitrophenyl)-2,2′-dithiazolylamine (VIII), yellow needles, m. 252-3\u00b0 [N-Ac derivative, yellow needles, m. 296-8\u00b0 (decomposition)]. Heating 4.5 g. I and 9.6 g. CH2<\/sub>ClCHClOEt in 50 cc. EtOH 1 hr. on a water bath gives 29.2% 2-thiazolylthiourea-HCl, clusters of felted needles, m. 203-4\u00b0 (decomposition); from the mother liquor 3.5 g. II is isolated. Heating 5.4 g. I and 7.4 g. CH2<\/sub>ClOMe 1 hr. on a water bath gives a mixture of 4-methyl-2-thiazolylthiourea (IX).HCl and IV.HCl which are separated by fractional crystallization from EtOH. Decomposition of IX.HCl with NaOAc gives IX, small rods, m. 174-5\u00b0. Treating 1.8 g. II in 25 cc. concentrated H2<\/sub>SO4<\/sub> at -5\u00b0 dropwise with 2 cc. concentrated HNO3<\/sub> in 10 cc. concentrated H2<\/sub>SO4<\/sub> and, after 2 hrs., pouring the mixture onto ice yield 85% 5,5′-dinitro-4,4′-dimethyl-2,2′-dithiazolylamine, small orange-red rods, decompose 233\u00b0; it dissolves in alc. NaOH with a deep red color. Similar nitration of 3.6 g. VI in 150 cc. boiling Me2<\/sub>CO with 10 cc. concentrated H2<\/sub>SO4<\/sub> and concentrated HNO3<\/sub> (1:1) gives 86% 5,5′-dinitro-4,4′-diphenyl-2,2′-thiazolylamine (X), orange-red leaflets, m. 229-31\u00b0 (decomposition); it crystallizes with 1 mole C5<\/sub>H5<\/sub>N, deep red rods. Adding Zn dust in small portions to 4.25 g. X in 25 cc. Ac2<\/sub>O and 10 cc. AcOH, refluxing the mixture 0.5 hr., pouring the filtered solution into H2<\/sub>O, and recrystallizing the precipitate from AcOH yield 5,5′-diamino-4,4′-diphenyl-2,2′-dithiazolylamine pentaacetate, rhombs, m. 208-9\u00b0. Treating 11.4 g. VIII with 100 cc. concentrated HNO3<\/sub> and warming the mixture on a water bath give 2.1 g. O2<\/sub>NC6<\/sub>H4<\/sub>CO2<\/sub>H, m. 141-2\u00b0; similarly, X yields BzOH.<\/p>\n

Chemische Berichte published new progress about 23286-70-6. 23286-70-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Amine,Ester, name is Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate, and the molecular formula is C7H11N3O2, Category: pyrazoles-derivatives<\/a>.<\/p>\n

Referemce:
https:\/\/en.wikipedia.org\/wiki\/Pyrazole<\/a>,
Pyrazoles – an overview | ScienceDirect Topics<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"

Chemische Berichte published new progress about 23286-70-6. 23286-70-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Amine,Ester, name is Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate, and the molecular formula is C7H11N3O2, Category: pyrazoles-derivatives<\/a>.<\/p>\n","protected":false},"author":8,"featured_media":0,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[131],"tags":[717],"class_list":["post-11127","post","type-post","status-publish","format-standard","hentry","category-pyrazoles-derivatives","tag-m-w150-200"],"yoast_head":"\nBeyer, Hans's team published research in Chemische Berichte in 89 | CAS: 23286-70-6 | pyrazoles-derivatives<\/title>\n<meta name=\"description\" content=\"Beyer, Hans published the artcileThiazoles. 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