Preparation of N-substituted amidines was written by Cooper, F. C.;Partridge, M. W.. And the article was included in Journal of the Chemical Society in 1953.Application of 5203-15-6 This article mentions the following:
PhNH2 (I) (10.1 g.), 25.4 g. 4-MeC6H4CN (II), 5 g. powd. Na, and 100 cc. PhMe-free C6H6 (III) refluxed 3 days and worked up as described by Lottermoser [J. prakt. Chem. 54, 113(1896)] gave 95% 4-MeC6H4C(:NH)NHPh (IV) (analyses indicated 88% CN– and 75% PhMe based on the equation: 2 RCN + ArNH2 + 2 Na â?RC(:NAr)NH– Na+ + RH + NaCN). I (20.2 g.), 25.4. g. II, 5 g. powd. Na, and 100 mL. III as in the previous example gave 96% IV and 0.5% kyanphenin (V). I (9.3 g.), 3.9 g. finely powd. NaNH2 and 100 cc. C6H6 refluxed about 1.25 h., 10.3 g. PhCN (VI) added, and the whole refluxed 2.25 h. gave 12.6 g. PhC(:NH)NHPh (VII), m. 114-15°; with granular NaNH2, the yield of VII was 57%, and with PhNMe2 as solvent, 23%. I (9.3 g.), 2.3 g. Na, 10.3 g. VI, and 100 cc. dry C6H6 refluxed 27 h. evolved no permanent gas; the products were VII, PhCH2NH2 (VIII) (identified as benzylammonium picrate), and BzH; I and Na in boiling C6H6 gave about 2% PhNHNa; VII and Na in boiling C6H6 gave no permanent gas and small amounts of VIII and I; I and VI refluxed 8 h. gave a trace of PhC(:NPh)NHPh. Two procedures were used to prepare the following compounds in procedure A, 0.1 mol each of powd. Na, the amine, and the nitrile in 100 cc. dry C6H6 were refluxed 20-30 h., 15 cc. EtOH was added, the base extracted into aqueous MeCH(OH)CO2H, isolated by addition of aqueous NH3, and crystallized from petr. ether; in Procedure B, granular NaNH2 was used in place of the Na of Procedure A (R, R’ in RC(:NH)NHR’, procedure, % yield, m. p., and m.p. of picrate): 4-MeC6H4, Ph, A, 65, 151-2°, 152-3°; 4-MeOC6H4, Ph, A, 51, 147-8°, 129-30°; 4-ClC6H4, Ph, A, 64, 140-1°, 175-6°; 4-sec-BuOC6H4, Ph, A, 63, 116.0-16.5°, 138-40°; Ph, 2-MeC6H4, A, 61, 109-10°, 152-3°; Ph, 4-MeOC6H4, A, 73, 115.5-16.5°, 171-3°; Ph, 2-C10H7, A, 39 (Procedure B gave 54%), 128.5-9.5°, 216.5-18.0°; Ph, 2-C5H4N, A, 65, 98.5-9.5°, 206-7°; Ph, cyclohexyl, A, 43, 115-16°, 142-3°; 2-MeC6H4, Ph, B, 47 122-3°, 175-6°; 4-PhOC6H4, Ph, A, 83, 183.5-4.5°, 145-6°; Ph, 2-thiazolyl, B, 6, 90-1°, 162-3°; PhCH2, Ph, B, 64, 140-1°, 109-10°; Me, Ph, B, 36, -, 190-1°; 2-phenylbenzimidazole, B, 72, 299-301°, 275-6° (decomposition). The following were prepared incidental to the above: p-ClC6H4NHCPh:NH.HCl.2H2O, needles, m. 103-6° (decomposition) (from H2O) {base, m. 114-15° [acetate, needles, m. 131-2° (from C6H6); picrate, m. 180-1°]}; N-(2-hydroxyethyl)benzamidinium picrate, prisms, m. 140-2°, solidifies and remelts at 180-215° (decomposition); 4-sec-BuOC6H4CN, b1.3 109-11°, n20D 1.5256; 4-HOC6H4(NHPh):NH.HO3SPh, m. 180-2°, (picrate, m. 82-4° (from aqueous iso-PrOH), base, small needles, m. 182.5-3.0°). In the experiment, the researchers used many compounds, for example, 4-iso-Butoxybenzonitrile (cas: 5203-15-6Application of 5203-15-6).
4-iso-Butoxybenzonitrile (cas: 5203-15-6) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Application of 5203-15-6
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts