{"id":11657,"date":"2022-12-01T06:40:04","date_gmt":"2022-11-30T22:40:04","guid":{"rendered":"https:\/\/www.pyrazoles-derivatives.com\/?p=11657"},"modified":"2022-12-01T06:40:04","modified_gmt":"2022-11-30T22:40:04","slug":"reimlinger-hans-k-s-team-published-research-in-chemische-berichte-in-94-cas-3553-12-6","status":"publish","type":"post","link":"https:\/\/www.pyrazoles-derivatives.com\/?p=11657","title":{"rendered":"Reimlinger, Hans K.’s team published research in Chemische Berichte in 94 | CAS: 3553-12-6"},"content":{"rendered":"

Reimlinger, Hans K. published the artcile3(5)-Diazopyrazole<\/i><\/b>, Application In Synthesis of 3553-12-6<\/a>, the publication is Chemische Berichte (1961), 1036-41, database is CAplus.<\/p>\n

3(5)-Aminopyrazole (I) prepared from pyrazole-3(5)-carboxylic acid hydrazide (II) gave with iso-AmONO the diazonium chloride (III). The diazotization in weakly acidic solution yielded the diazoamino compound III was converted in weakly alk. solution to the CHCl3<\/sub>-soluble unstable 3(5)-diazopyrazole (IV). III and IV gave with HI the 3(5)-iodopyrazole (V) and with 2-C10<\/sub>H7<\/sub>OH (VI) an O-free coupling product. Et 3(5)-pyrazolecarboxylate (342 g.) (from 300 g. N2<\/sub>CHCO2<\/sub>Et and C2<\/sub>H2<\/sub>) in 200 g. anhydrous N2<\/sub>H4<\/sub> heated 8 h. on the water bath and evaporated in vacuo yielded 390 g. II, m. 166-8\u00b0 (MeOH). II (390 g.) in 2.5 l. 2N HCl treated with stirring at 0\u00b0 with solid NaNO2<\/sub> in small portions gave 340 g. pyrazole-3(5)-carboxylic acid azide (VII), m. 158-60\u00b0. VII (340 g.) in 500 cc. absolute EtOH heated 24 h. on the water bath gave 299 g. Et N-[3(5)-pyrazolyl]urethane (VIII), m. 155-7\u00b0 (MeOH). VIII (299 g.) and 920 g. Ba(OH)2<\/sub>.8H2<\/sub>O in 1.6 l. H2<\/sub>O refluxed 36 h., filtered, concentrated to half-volume, and extracted continuously with Et2<\/sub>O yielded 127 g. I, b1.5<\/sub> 115-16\u00b0, m. 38-40\u00b0. VIII (10 g.), 20 cc. concentrated HCl, and 10 cc. AcOH refluxed 10 h., evaporated in vacuo, the viscous residue dissolved in saturated aqueous Na2<\/sub>CO3<\/sub>, and the solution extracted continuously with Et2<\/sub>O yielded 5.3 g. N-Ac derivative of I, m. 22-3\u00b0 (dioxane). I (3 g.) in 150 cc. MeOH saturated at 0\u00b0 with HCl, filtered, the residue in 100 cc. MeOH treated during 5 min. with dry HCl and then with stirring at 0\u00b0 with 10% excess iso-AmONO, and the mixture diluted after 1.5 h. with 250 cc. Et2<\/sub>O gave III, decomposed at 180-5\u00b0. I (3 g.) in 150 cc. 85% H3<\/sub>PO4<\/sub> treated with stirring at 0\u00b0 slowly with concentrated aqueous NaNO2<\/sub> and then with saturated aqueous NaOAc yielded 3(5),3′(5′)-diazoaminopyrazole, C6<\/sub>H7<\/sub>N7<\/sub>, yellowish crystals, decomposed at 186-7.5\u00b0 (MeOH-NH4<\/sub>OH). III (0.7 g.) in CHCl3<\/sub> adjusted at 0\u00b0 with 50 cc. saturated aqueous Na2<\/sub>CO3<\/sub> to pH 8, the aqueous phase extracted with CHCl3<\/sub>, and the CHCl3<\/sub> solution evaporated cold in vacuo gave long needles of IV, which decomposed rapidly at room temperature with the formation of brown insoluble products. III (1 g.) in 150 cc. CHCl3<\/sub> treated at -10\u00b0 with 3 cc. Et3<\/sub>N gave a solution of IV. IV in solution treated carefully with CHCl3<\/sub> saturated with HCl yielded III. III (from 4 g. I) in a little H2<\/sub>O treated at 0\u00b0 with 7 g. NaI in 150 cc. H2<\/sub>O, the mixture heated 0.5 h. on the water bath, evaporated in vacuo, and the residue extracted with Et2<\/sub>O yielded 6% V, needles, m. 72-3\u00b0 (H2<\/sub>O). IV (from 1.2 g. I) in CHCl3<\/sub> treated at 0\u00b0 with 4 g. 68% HI, the mixture warmed to room temperature, and worked up in the usual manner gave V. A solution of III (from 3.5 g. I added dropwise at 0\u00b0 to 12.5 g. VI in 10% aqueous NaOH) gave 2.8 g. coupling product, C13<\/sub>H8<\/sub>N4<\/sub>, yellow needles from much H2<\/sub>O, yellow-red platelets from aqueous MeOH, m. 192-4\u00b0; the filtrate gave addnl. product. IV solution from III in CHCl3<\/sub> treated with concentrated VI in CHCl3<\/sub> and evaporated also gave the coupling product, yellow-red leaflets, m. 192-4\u00b0 (aqueous MeOH). The UV and IR absorption spectra of III and IV were recorded.<\/p>\n

Chemische Berichte published new progress about 3553-12-6. 3553-12-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Amine,Amide, name is 3-Acetamidopyrazole, and the molecular formula is C5H7N3O, Application In Synthesis of 3553-12-6<\/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 3553-12-6. 3553-12-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Amine,Amide, name is 3-Acetamidopyrazole, and the molecular formula is C5H7N3O, Application In Synthesis of 3553-12-6<\/a>.<\/p>\n","protected":false},"author":8,"featured_media":0,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[814,131],"tags":[732],"class_list":["post-11657","post","type-post","status-publish","format-standard","hentry","category-3553-12-6","category-pyrazoles-derivatives","tag-m-w100-150"],"yoast_head":"\nReimlinger, Hans K.'s team published research in Chemische Berichte in 94 | CAS: 3553-12-6 | pyrazoles-derivatives<\/title>\n<meta name=\"description\" content=\"Reimlinger, Hans K. published the artcile3(5)-Diazopyrazole, Application In Synthesis of 3553-12-6, the publication is Chemische Berichte (1961), 1036-41, database is CAplus.\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.pyrazoles-derivatives.com\/?p=11657\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Reimlinger, Hans K.'s team published research in Chemische Berichte in 94 | CAS: 3553-12-6 | pyrazoles-derivatives\" \/>\n<meta property=\"og:description\" content=\"Reimlinger, Hans K. published the artcile3(5)-Diazopyrazole, Application In Synthesis of 3553-12-6, the publication is Chemische Berichte (1961), 1036-41, database is CAplus.\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.pyrazoles-derivatives.com\/?p=11657\" \/>\n<meta property=\"og:site_name\" content=\"pyrazoles-derivatives\" \/>\n<meta property=\"article:published_time\" content=\"2022-11-30T22:40:04+00:00\" \/>\n<meta name=\"author\" content=\"Jessica.F\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Jessica.F\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"3 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\/\/schema.org\",\"@graph\":[{\"@type\":\"WebPage\",\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/?p=11657\",\"url\":\"https:\/\/www.pyrazoles-derivatives.com\/?p=11657\",\"name\":\"Reimlinger, Hans K.'s team published research in Chemische Berichte in 94 | CAS: 3553-12-6 | pyrazoles-derivatives\",\"isPartOf\":{\"@id\":\"http:\/\/www.pyrazoles-derivatives.com\/#website\"},\"datePublished\":\"2022-11-30T22:40:04+00:00\",\"author\":{\"@id\":\"http:\/\/www.pyrazoles-derivatives.com\/#\/schema\/person\/d9a9f27bed675392c6f363a01ffd49f1\"},\"description\":\"Reimlinger, Hans K. published the artcile3(5)-Diazopyrazole, Application In Synthesis of 3553-12-6, the publication is Chemische Berichte (1961), 1036-41, database is CAplus.\",\"breadcrumb\":{\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/?p=11657#breadcrumb\"},\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"ReadAction\",\"target\":[\"https:\/\/www.pyrazoles-derivatives.com\/?p=11657\"]}]},{\"@type\":\"BreadcrumbList\",\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/?p=11657#breadcrumb\",\"itemListElement\":[{\"@type\":\"ListItem\",\"position\":1,\"name\":\"\u9996\u9875\",\"item\":\"http:\/\/www.pyrazoles-derivatives.com\/\"},{\"@type\":\"ListItem\",\"position\":2,\"name\":\"Reimlinger, Hans K.’s team published research in Chemische Berichte in 94 | CAS: 3553-12-6\"}]},{\"@type\":\"WebSite\",\"@id\":\"http:\/\/www.pyrazoles-derivatives.com\/#website\",\"url\":\"http:\/\/www.pyrazoles-derivatives.com\/\",\"name\":\"pyrazoles-derivatives\",\"description\":\"Several pyrazole derivatives possess important pharmacological activities and they have been proved useful materials in drug research. 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