{"id":12086,"date":"2023-01-30T07:04:01","date_gmt":"2023-01-29T23:04:01","guid":{"rendered":"https:\/\/www.pyrazoles-derivatives.com\/?p=12086"},"modified":"2023-01-30T07:04:01","modified_gmt":"2023-01-29T23:04:01","slug":"gilman-h-et-al-published-their-research-in-journal-of-the-american-chemical-society-in-1946-cas-401-73-0","status":"publish","type":"post","link":"https:\/\/www.pyrazoles-derivatives.com\/?p=12086","title":{"rendered":"Gilman, H. et al. published their research in Journal of the American Chemical Society in 1946 | CAS: 401-73-0"},"content":{"rendered":"

Compounds containing the trifluoromethyl group was written by Gilman, H.;Tolman, L.;Yeoman, F.;Woods, L. A.;Shirley, D. A.;Avakian, S.. And the article was included in Journal of the American Chemical Society in 1946.Formula: C4H3F3N2O<\/a> This article mentions the following:<\/p>\n

The following compounds were prepared as possible antimalarials. Of the compounds tested only m-(trifluoromethyl)benzenearsonic acid (I) showed activity but the specific contribution of the F3<\/sub>C group to such action is uncertain. m-F3<\/sub>CC6<\/sub>H4<\/sub>N2<\/sub>Cl (0.0163 mole), added to a cold solution of 0.0163 mole of 2-hydroxydibenzofuran in KOH (temperature below 5\u00b0) with stirring for 30 min., give 46-50% of 1-(m-trifluoromethylphenylazo)-2-hydroxydibenzofuran, red, m. 173-4\u00b0; 2,8-dihydroxydibenzofuran gives 15-20% of the 2,5-di-HO derivative, orange-brown, m. 256-7\u00b0. m-F3<\/sub>CC5<\/sub>H4<\/sub>Br (Simons and Ramler, C.A. 37, 2341.8) has nD<\/sub>20<\/sup> 1.4749, d27<\/sub>29<\/sup> 1.606 (55% yield); the Grignard reagent yields 52-9% of m-(trifluoromethyl)benzaldehyde (II), b10<\/sub> 64-6\u00b0, nD<\/sub>20<\/sup> 1.4660, d27<\/sub>29<\/sup> 1.300; 2,4-dinitrophenylhydrazone, yellow, m. 259-60\u00b0. II (5.48 g.) and 5.3 g. m-F3<\/sub>CC6<\/sub>H4<\/sub>NH2<\/sub> in 50 cc. C6<\/sub>H6<\/sub>, refluxed 5 hrs., give 62% of N-(m-trifluoromethylbenzylidene)-m-(trifluoromethyl)aniline, m. 50-1\u00b0. II yields 65% of an oxime, b12<\/sub> 102-4\u00b0, nD<\/sub>20<\/sup> 1.5128, d27<\/sub>29<\/sup> 1.305. p-H2<\/sub>NC6<\/sub>H4<\/sub>NHAc (25 g.) and 19 g. (CH2<\/sub>Ac)2<\/sub>, heated on the steam bath for 1 hr., give 73% of N-(p-acetamidophenyl)-2,5-dimethylpyrrole, m. 207-8\u00b0. 4-Dibenzofuraldehyde yields a 2,4-dinitrophenylhydrazone, yellow, m. 301-2\u00b0. II (0.95 g.) and 1 g. 4-aminodibenzofuran in C6<\/sub>H6<\/sub>, refluxed 1 hr. and the residual red oil heated at 120-30\u00b0 for 1 hr., give 29% of 4-(m-trifluoromethylbenzylideneamino)dibenzofuran, m. 81-3\u00b0. m-F3<\/sub>CC6<\/sub>H4<\/sub>NH2<\/sub> (10 g.), 11.5 g. Et2<\/sub>N(CH2<\/sub>)3<\/sub>Cl, and a trace of Cu, heated 5 hrs. at 135-40\u00b0, give 27% of m-(3-diethylaminopropylamino)(trifluoromethyl)benzene, light yellow, b23<\/sub> 171-5\u00b0. m- F3<\/sub>CC6<\/sub>H4<\/sub>N2<\/sub>Cl yields 51% of I, m. 137-8\u00b0. 3,6-H2<\/sub>N(O2<\/sub>N)C6<\/sub>H3<\/sub>CF3<\/sub> (Rouche, C.A. 22, 2149) (41 g.), 29 g. H3<\/sub>AsO3<\/sub>, and 53 g. C3<\/sub>H5<\/sub>(OH)3<\/sub>, added to 56 g. concentrated H2<\/sub>SO4<\/sub>, stirred 2 hrs., and refluxed 2 hrs., give 56% of 6-nitro-7-(trifluoromethyl)quinoline, m. 164-5\u00b0; reduction with SnCl2<\/sub>-concentrated HCl gives 92% of the 6-NH2<\/sub> derivative (III), m. 154-5\u00b0. III (5 g.) and (CH2<\/sub>Ac)2<\/sub> in 10 cc. EtOH and 1 drop concentrated HCl, refluxed 22 hrs., give 46% of 6-(2,5-dimethylpyrryl)-7-(trifluoromethyl)quinoline, b1<\/sub> 135-8\u00b0, m. 86-7\u00b0. F3<\/sub>CCH2<\/sub>COCH2<\/sub>CO2<\/sub>Et (10 g.) and 2.6 cc. N2<\/sub>H4<\/sub>.H2<\/sub>O in 20 cc. hot H2<\/sub>O give 46.3% of 3-trifluoromethyl-5-pyrazolone, m. 208.5-9.2\u00b0. In the experiment, the researchers used many compounds, for example, 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0Formula: C4H3F3N2O<\/a>).<\/p>\n

3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0) belongs to pyrazole derivatives. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugated acid 2.49 at 25 \u00b0C).Pyrazole used as a ligand to prepare organometallic compounds. Pyrazole the presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Formula: C4H3F3N2O<\/a><\/p>\n

Referemce:
Pyrazole – Wikipedia<\/a>,
Pyrazoles – an overview | ScienceDirect Topics<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"

3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0) belongs to pyrazole derivatives. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugated acid 2.49 at 25 \u00b0C).Pyrazole used as a ligand to prepare organometallic compounds. Pyrazole the presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Formula: C4H3F3N2O<\/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":[128],"class_list":["post-12086","post","type-post","status-publish","format-standard","hentry","category-pyrazoles-derivatives","tag-100-200"],"yoast_head":"\nGilman, H. et al. published their research in Journal of the American Chemical Society in 1946 | CAS: 401-73-0 | pyrazoles-derivatives<\/title>\n<meta name=\"description\" content=\"Compounds containing the trifluoromethyl group was written by Gilman, H.;Tolman, L.;Yeoman, F.;Woods, L. A.;Shirley, D. A.;Avakian, S.. 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