1,2,4-Triazine 33-dichloro

In connection with the biological activity of s-triazines, Burchfield and Storrs investigated the reaction of 2,4-dichloro-6-(o-chloro-anilino)-s-triazine with over sixty amino acids, peptides, and related... 

In this solvent the reaction is catalyzed by small amounts of trimethyl-amine and especially pyridine (cf. 9). The same effect occurs in the reaction of iV -methylaniline with 2-iV -methylanilino-4,6-dichloro-s-triazine. In benzene solution, the amine hydrochloride is so insoluble that the reaction could be followed by recovery. of the salt. However, this precluded study mider Bitter and Zollinger s conditions of catalysis by strong mineral acids in the sense of Banks (acid-base pre-equilibrium in solution). Instead, a new catalytic effect was revealed when the influence of organic acids was tested. This was assumed to depend on the bifunctional character of these catalysts, which act as both a proton donor and an acceptor in the transition state. In striking agreement with this conclusion, a-pyridone is very reactive and o-nitrophenol is not. Furthermore, since neither y-pyridone nor -nitrophenol are active, the structure of the catalyst must meet the conformational requirements for a cyclic transition state. Probably a concerted process involving structure 10 in the rate-determining step... 

Reagent P-K a 2-Chloro- pyrimidine 2-Chloro- 3-nitro- pyridine 2-Chloro- 5-nitro- pyridine 2,4-Dichloro- phenylamino-s-triazine ... 

Series 2-amino-4,6-dichloro-s-triazine k in liter x mole i x min i. Ref. 27. 

Sodium methyl mercaptide in xylene was reported to react (25°, 2 hr) in a stepwise fashion with 3,5-dichloro-as-triazine to yield the 3-methylthio-5-chloro and then (70°, 2 hr) the 3,5-bis-methylthio derivatives. However, the structure of the former is very likely to be 307. With dimethylamine in benzene (25°, 5 min), ethyleneimine in ether (25°, 3 min), and alcoholic ammonia (25°, few min), this dichloro derivative was assumed to form 3-amino derivatives. The high reactivity of as-triazines is demonstrated by the facile ethoxylation... 

Dichloro-s-triazine and its 6-alkyl analogs are as easily hydrolyzed by water as trichloro-s-triazine and, on suspension in aqueous ammonia (25°, 16 hr), the first is diaminated in good yield. 2,4-Bistrichloromethyl-6-methyl- and -6-phenyl-s-triazines (321) require a special procedure for mono-alkoxylation (0-20°, 16 hr, alcoholic triethylamine) disubstitution occurs at reflux temperature (8 hr). Aqueous triethylamine (100°, 3 hr) causes complete hydroxy-lation of 2,4,6-tris-trichloromethyl-s-triazine which can be mono-substituted with ammonia, methylamine, or phenoxide ion at 20°. 

Azide ion is a rather weak nitrogen nucleophile, but in aqueous acetone (20°, 5 min) it readily produces 2-azido-4,6-dichloro-s-triazine (330) and also yields more slowly (0°, 12 hr, 90% yield) the 2,4,6-triazido-s-triazine. The latter is rapidly hydrolyzed (50°) to cyanuric acid and is easily mono-aminated (0°, 1 hr, in ether). 

Because of the high polarity of the C=N double bonds, cyanuric chloride (120, R= Cl) is comparable with a carboxylic acid chloride. This explains its smooth reaction with diazomethane to yield dichloro-(diazomcthyl)-l,3,5-triazine (121, R = The analogous com-... 

OCH, BPA 2-methoxy-4,6- dichloro-S-triazine Cetyldimethyl ammonium choloride CHCI3 5 5 — 0.80 (CHC13) 80... 

The NH2 groups can be diazotized and reduced in the presence of thiosulphates and different metal ions. The effect of some metal ions, namely Fe ", Sn, Cu +, and Co on the graft yield of cotton modified with aryl diazonium groups via its reaction with 2,4-dichloro-6-(p-nitroaniline)-5-triazine in the presence of alkali and followed by reduction of nitro group was studied [4]. 

Tricyclic 84 was prepared [91JCS(P1)1762] by the thermal intramolecular rearrangement of dichloro(pyrrolidinylcycloheptenyl)triazine 83. Its structure was confirmed by X-ray crystallography (Scheme 21). 

Sodium chlorocyanurate l,3-dichloro-l,3,5-triazine-2,4,6(lH,3H, 5H)-trione sodium salt SDIC... 

Dichlorotetrafluoroethane (Refrigerant 114) Dichloro-5-triazine-2,4,6-trione, sodium salt Oichlorovos Dieldrin... 

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