Substituted Chlorodiamino-s-triazines¹

Abstract

Vol. 70 from 250 cc. of hot ethanol. The yield of pure product was 1 g., m. p. 185-188°dec.Anal. Calcd. for C22H39O6NS: N, 3.14. Found: N (Dumas), 2.84, basic N (perchloric acid titration in acetic acid), 2.76.The product was soluble in sodium bicarbonate solutions and in hot dilute hydrochloric acid solution. Alkaline titration indicated the presence of one carboxyl and one lactone group. The reaction product obtained from cysteine and Afl.r-angelicalactone11 when titrated with perchloric acid showed the absence of a basic amino group; protolichesterinic acid appears to have added cysteine through the -SH group without secondary involvement of the amino group. Antibacterial Tests.-Tests against the Streptococcus, Staphylococcus and Bacillus typhi were conducted in tryptose phosphate medium. The inoculum was a 1:1000 dilution of a twenty-four-hour culture of the organism and incubation was for eighteen hours at 37°. The anaerobe was tested in Bacto-Anaerobe Medium with Dextrose. The acid-fast organisms, B. tuberculosis ranae and the human tuberculosis strain H37Rv were grown in submerged culture in Youmans' modification14 of Proskauer-Beck synthetic medium. The inoculum with ranae was a (14) Composition: Asparagin, 0.5%; primary potassium acid phosphate, 0.5%, potassium sulfate, 0.05%; magnesium citrate, 0.15%; and glycerol, 2% in distilled water.1:100 dilution of a forty-eight hour culture in Long's synthetic medium; incubation was for forty-eight hours at 37°. An inoculum of 0.02 mg. of fresh bacteria per cc. of test medium was used with H37Rv; incubation at 37°w as for fourteen days, excellent growth being evidenced after eight days.Acknowledgment.-We are indebted to M. E. Auerbach and Staff for analytical data, to Dr. F. C. Nachod for surface-tension measurements, and John W. Klimek for antifungal tests.

Labelled compounds of interest as antitumour agents – VIII. Synthesis of 2H‐isotopomers of pentamethylmelamine and of a potential prodrug thereof

“…16 However, this process cannot be adapted to the preparation of the trideuteropentamethylmelamine isotopomer 3b from 4,6-bis(dimethylamino)-1,3,5-triazin-2-amine, as over-alkylation to hexamethylmelamines can result from prototropic equilibration of the intermediate anions. However, treatment of the chlorotriazine 5 17 with one equivalent of trideuteromethylamine in hot basic aqueous solution afforded the required pentamethylmelamine isotopomer 3b in good yield (Scheme 1). The NMR spectra of 3b confirmed the location of the deuterium atoms.…”

Effect of Few Parameters on Removal of Atrazine from Waste Water

“…Gaseous cyanogen chloride was trimerized to cyanuric chloride in presence organic solvents like carbon tetrachloride, ethyl ether or benzene. Hydrogen chloride was used as a catalyst (Pearlman, 1948). Currently atrazine is synthesized by reaction given in Figure 1.…”

Synthesis of polynuclear heterocyclic polynitrogen systems based on cyanuric chloride and its derivatives

“…In a continuation of these investigations in the present work we have examined a version of the synthesis of polynuclear structures based on the molecules of cyanuric chloride (1), 2-chloro-4,6-dimethoxy-1,3,5-triazine (2), 2-chloro-4,6-dimorpholino-1,3,5-triazine (3), 2,4-dichloro-6-methoxy-1,3,5-triazine (4), and 2,4-dichloro-6-diethylamino-1,3,5-triazine (5). As known, cyanuric chloride readdily enters into reaction with various nucleophiles [3,4]. It was assumed that this compound and its derivatives would react no less vigorously with azoles, forming polynuclear structures.…”