{"id":10349,"date":"2022-10-20T04:13:01","date_gmt":"2022-10-19T20:13:01","guid":{"rendered":"https:\/\/www.pyrazoles-derivatives.com\/?p=10349"},"modified":"2022-10-20T04:13:01","modified_gmt":"2022-10-19T20:13:01","slug":"owen-l-n-s-team-published-research-in-journal-of-the-chemical-society-in-1947-cas-15366-34-4","status":"publish","type":"post","link":"https:\/\/www.pyrazoles-derivatives.com\/?p=10349","title":{"rendered":"Owen, L. N.&#8217;s team published research in Journal of the Chemical Society in 1947 | CAS: 15366-34-4"},"content":{"rendered":"<p>In 1947,Owen, L. N.; Somade, H. M. Babatunde published \u300aOlefinic acids. II. Reactivity of \u03b1-bromoacrylic acid and some related compounds\u300b.Journal of the Chemical Society published the findings.<a href=\"https:\/\/www.ambeed.com\/products\/15366-34-4.html\">Electric Literature of C5H6N2O2<\/a> The information in the text is summarized as follows:<\/p>\n<p>cf. C.A. 39, 4589.1. BrCH2CHBrCO2H (I) (24 g.) in 20 cc. MeOH and 11 cc. 3.76 N MeOH-MeONa, refluxed 7 hrs., gives 1.1 g. \u03b2-methoxyacrylic acid (II), m. 102\u00b0, absorption maximum at 2280 A. (\u03b5 14,100); it yields malonic semialdehyde 2,4-dinitrophenylhydrazone (III), lemon-yellow, m. 136\u00b0 (decomposition); aqueous NaOH gives a deep red solution I (90 g.) in H2O, neutralized with N NaOH at 0\u00b0, treated with an equal volume N NaOH, and kept at room temperature 1 hr., gives 87% CH2:CBrCO2H (IV), m. 72\u00b0, stable for several months. IV (15 g.) in 40 cc. MeOH and 35 cc. 3.67 N MeOH-MeONa, refluxed 3 hrs., give a liquid acid containing some II; with MeI and Ag2O in ether, refluxed 0.5 hr., the acid yields MeOCH2CHBrCO2Me containing some MeOCH2CH(OMe)CO2Me. IV (10 g.) and 45 cc. 2 N EtOH-EtONa, refluxed 20 hrs., give 1 g. EtOCH:CHCO2H, m. 109\u00b0, absorption maximum at 2300 A. (\u03b5 14,700); ether extraction of the aqueous solution gives 5.1 g. of a liquid halogen-free acid which, with EtI and Ag2O, gives 1.5 g. Me \u03b1,\u03b2-diethoxypropionate, b11 87\u00b0, nD21 1.4130. IV (7.5 g.) in 60 cc. iso-PrOH and 5 g. K in 60 cc. iso-PrOH, refluxed 24 hrs., give 7 g. of mainly \u03b2-isopropoxyacrylic acid (probably containing 12% iso-PrOCH:C(OPr-iso)CO2H), b0.001 55\u00b0, nD15 1.4425, absorption maximum at 2340 A., \u03b5 14,000; 2,4-(O2N)2C6H3NHNH2 gives III; neither acid could be purified. IV (15.2 g.) in 20 cc. tert-BuOH and 10 g. K in 200 cc. tert-BuOH, refluxed 24 hrs., give 4.9 g. \u03b2-tert-butoxyacrylic acid, m. 86.5\u00b0, absorption maximum at 2370 A., \u03b5 15,400. CH2:C(OMe)CO2Me (b15 58-60\u00b0, absorption maximum at 2280 A., \u03b5 7300) (2.1 g.) and 15 cc. 2 N NaOH, heated 1.5 hrs. at 100\u00b0, give 1.2 g. \u03b1-methoxyacrylic acid (V), m. 52\u00b0, absorption maximum at 2280 A., \u03b5 6000; V is unchanged on refluxing 6 hrs. with N MeOH-MeONa; EtOCH:CHCO2H behaves similarly. IV (5 g.), added to 5 cc. AcSH cooled in ice and heated 15 min. on the steam bath, gives 6.9 g. \u03b1-bromo-\u03b2-(acetylmercapto)-propionic acid, m. 85-6\u00b0; the \u03b1-Cl analog m. 75\u00b0; under the same conditions MeCH:CBrCO2H (VI) is unchanged. IV (0.5 g.), 0.5 cc. C5H5N, and 1 cc. PhCH2SH, heated 15 min. on the steam bath, give \u03b2-(benzylmercapto)-acrylic acid, m. 162-3\u00b0, absorption maximum at 2740 A., \u03b5 15,500. IV (2 g.) in excess CH2N2 in ether, kept 5 days at 20\u00b0 and the liquid residue heated to 60\u00b0, gives 0.9 g. Me 3-pyrazolecarboxylate (VII), m. 141\u00b0; CH2:CClCO2H gives the same product; VI gives the 4-Me derivative of VII, m. 170\u00b0. Me2C:CBrCO2H (2 g.) and CH2N2 give 1.8 g. Me \u03b1-bromo-\u03b2,\u03b2-dimethylacrylate, b9 76\u00b0, nD21 1.4909; NH4OH gives \u03b1-bromo-\u03b2,\u03b2-dimethylacrylamide, m. 129\u00b0. CH2:CBrCO2Me (1 g.) and 2 g. N2CHCO2Me in petr. ether (b. 80-100\u00b0), refluxed 15 hrs., give 1.3 g. di-Me 3,5-pyrazoledicarboxylate, m. 152\u00b0. The Me ester of VI (1 g.) and 1 g. N2CHCO2Me in petr. ether, refluxed 24 hrs., give 0.15 g. di-Me 4-methyl-3,5-pyrazoledicarboxylate, m. 128-9\u00b0. Me2C:CBrCO2H does not react with N2CHCO2Me. CH2:C(OMe)CO2Me (VIII) and CH2N2 in ether, kept 4 days at 20\u00b0, give a liquid b. about 135\u00b0; NH4OH gives 1-methoxy-1-cyclopropanecarboxamide, m. 117\u00b0. VIII in MeOH, saturated with dry HCl at 0\u00b0, gives MeC(OMe)2CO2Me.Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4<a href=\"https:\/\/www.ambeed.com\/products\/15366-34-4.html\">Electric Literature of C5H6N2O2<\/a>) was used in this study.<\/p>\n<p>Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4) belongs to pyrazoles. The application of pyrazole derivatives in the development of anticancer agents has been thoroughly investigated and verified. Moreover, the medicinal features of a number of natural products incorporating pyrazole moiety such as pyrazofurin, pyrazofurin B, pyrazole-3(5)-carboxylic acid and 4-methylpyrazole-3(5)-carboxylic acid have been reported.<a href=\"https:\/\/www.ambeed.com\/products\/15366-34-4.html\">Electric Literature of C5H6N2O2<\/a><\/p>\n<p>Referemce:<br \/><a href=\"https:\/\/en.wikipedia.org\/wiki\/Pyrazole\">Pyrazole &#8211; Wikipedia<\/a>,<br \/><a href=\"https:\/\/www.sciencedirect.com\/topics\/chemistry\/pyrazoles\">Pyrazoles &#8211; an overview | ScienceDirect Topics<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4) belongs to pyrazoles. The application of pyrazole derivatives in the development of anticancer agents has been thoroughly investigated and verified. Moreover, the medicinal features of a number of natural products incorporating pyrazole moiety such as pyrazofurin, pyrazofurin B, pyrazole-3(5)-carboxylic acid and 4-methylpyrazole-3(5)-carboxylic acid have been reported.<a href=\"https:\/\/www.ambeed.com\/products\/15366-34-4.html\">Electric Literature of C5H6N2O2<\/a><\/p>\n","protected":false},"author":8,"featured_media":0,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[174,131],"tags":[128],"class_list":["post-10349","post","type-post","status-publish","format-standard","hentry","category-15366-34-4","category-pyrazoles-derivatives","tag-100-200"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v24.9 - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>Owen, L. 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