Thio amides. V. Preparation of some N-substituted p-alkoxythiobenzamides was written by Reynaud, Pierre;Moreau, Robert C.;Samama, Jean Paul. And the article was included in Bulletin de la Societe Chimique de France in 1965.HPLC of Formula: 5203-15-6 This article mentions the following:
A series of p-RC6H4NHC(S)C6H4OR1-p (I) was prepared as analogs of the antitubercular thioureas; in formula I, R is an alkoxy group, Me2N, or Cl, and R1 is Bu, iso-Bu, or iso-Am. p-NCC6H4OH (1 mole), 1 mole NaOEt, and 1.10 mole appropriate alkyl bromide refluxed 24 hrs. with stirring gave the corresponding p-ROC6H4CN (R, b.p./mm., n25D, and % yield given): Bu (II), 133°/0.3, 1.5351, 82; iso-Bu, 122°/0.3, 1.5350, 51; iso-Am, 155.5°/0.3, 1.5260, 80. II (27.5 g.) in 30 cc. CHCl3 and 15 g. absolute EtOH treated at about -5° with dry HCl to a weight increase of 7 g., kept 4 hrs. at -5°, and refrigerated 10 days, and the crystalline product treated at -20° in 200 cc. dry Et2O with stirring with dry NH3 yielded 80% p-BuOC6H4C(:NH)OEt (III), b0.05 118-19°, n25D 1.5315. Similarly were prepared p-iso-BuOC6H4C(:NH)OEt (IV), 88%, b0.05 122-5°, n25D 1.5282, and p-iso-AmOC6H4C(:NH)OEt (V), 89%, b0.05 123°, m, 25°, n25D 1.515. III (22.10 g.) and 35 g. dry C5H5N treated at about 0° with dry H2S to a weight increase of 7 g. and kept overnight yielded 23.2 g. yellow p-BuOC6H4C(S)OEt (VI), m. 71° (absolute EtOH). Similarly were prepared p-isoBuOC6H4C(S)OEt, 97%, b0.1 134-5°, m. 25°, and p-iso-AmOC6H4C(S)OEt, 100%, m. 53° (EtOH), from IV and V, resp. p-AcNHC6H4OH was converted by the method of Gutekunst and Gray (CA 16, 3089) to p-BuOC6H4NH2 (VII), b12 143-4° p-iso-BuOC6H4NH2, b10 145-6°, and p-iso-AmOC6H4NH2, b15 149-50°. VII (4.95 g.) in 15 cc. Et2O added dropwise with stirring to EtMgBr from 0.03 mole EtBr in 30 cc. dry Et2O, refluxed 15 min., treated with 3.57 g. VI in the min. amount Et2O, refluxed 1 hr., and evaporated, and the residue treated with 100 cc. HCl and ice gave 92% I (R = BuO, R1 = Bu), m. 152° (MeOH-C6H6); method A. VI (0.015 mole) treated similarly with the reaction mixture from p-Me2NC6H4NH2 and EtMgBr, and the residue decomposed with dilute iced HCl and extracted with Et2O yielded 94% I (R = Me2N, R1 = Bu), m. 154.5° (EtOH); method B. Similarly were prepared the following I (R1= Bu) (R, m.p., method and % yield, given): EtO, 155° (MePh), A, 90; iso-BuO, 164° (AcOEt), A, 95.2; AmO, 151° (MeOH-C6H6), A, 64; Cl, 185° (AcOEt), A, 89. Similarly were prepared the following I (R1 = iso-Bu) (same data given): EtO, 178° (MePh), A, 99; BuO, 164° (EtOH), A, 97; iso-BuO, 159° (AcOEt), A, 97; AmO, 149° (EtOH), A, 99; Cl, 210° (Me2CO), A, 87; Me2N, 173° (EtOH), B, 92. Similarly were prepared the following I (R1 = isoAm) (same data given): EtO, 162-3° (MePh), A, 99; BuO, 159° (EtOH), A, 87; iso-BuO, 164° (AcOEt), A, 95; AmO, 95° (AcOEt), A, 95; Cl, 194° (AcOEt), A, 90; Me2N, 159° (EtOH), B, 91. The ir spectra of III, V, AmC(:NH)OEt, and EtC(:NH)OEt are recorded and the ir maximum of III, IV, V, and PhC(:NH)OEt are tabulated. In the experiment, the researchers used many compounds, for example, 4-iso-Butoxybenzonitrile (cas: 5203-15-6HPLC of Formula: 5203-15-6).
4-iso-Butoxybenzonitrile (cas: 5203-15-6) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.HPLC of Formula: 5203-15-6
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts