Chloro-l,3,5-triazines

Giardina, M.C., Giardi, M.T, and Filacchioni, G. 4-Atnino-2-chloro-l, 3,5-triazine a new metabolite of atrazine by a soil bacterium, Agric. Biol Chem., 44 2067-2072, 1980. 

N -Cyanocarbamimides (112) may be condensed with chloromethyleniminium salts in a similar way (equation 58). Yields are good to excellent, and reaction conditions are mild (Table 12) (81S907). The synthesis provides an easy route to 4-aIkoxy-2-chloro-l,3,5-triazines (113) and the-corresponding mercapto derivatives. 

Diazo Components With Two Different Cationic Residues. Mono- and disazo dyes have been prepared in which the diazo compound carries at least two different basic and/or cationic groups.Reaction of 2,4- or 2,5-diaminobenzene sulfonic acids with 2-chloro-l,3,5-triazines that are substituted in positions 4 and 6 by aminoalk-ylamines and cyclic ammonium alkylamines, respectively, leads to diazo compo-... 

Case 26. 2-Chloro-l,3,5-triazines as Activating Groups of Carboxylic... 

The activation of carboxylic acids by means of 2-chloro-l,3,5-triazines 1 proceeds via triazinyl ammonium salts 2 that are formed in situ in flie presence of flie appropriate tertiary amine. The formation of salts 2 occurs by an addition-elimination SNAr mechanism and the reaction rates strongly depend on the steric hindrance of the substituents in the amine employed. 

Flament et al made use of the partial replacement of two chlorine atoms in cyanuric chloride (12) with methoxyl groups, the 2,4-di-methoxy-6-chloro-l,3,5-triazine (13) formed was dehalogenated to 2,4-dimethoxy-1,3,5-triazine (14) and this yielded the product (2) on gentle hydrolysis. 

The 11 NMR spectrum (500MHz) of 3-(4-chloro-phenyl)-7-ethyl-7,9-dimethyl-2,3,4,9-tetrahydropyrimido[l,2-tf]-[l,3,5]triazine-6,8-dione 49 <2002JHC663> showed the presence of quartets (AB pattern) at 6 4.99 and 6 5.12 corresponding to the methylene protons of the triazine ring. 

Because of the relatively low sensitivity of TLC methods they have not been frequently applied for the analysis of samples containing trace amounts of synthetic dyes. However, TLC techniques have been proven to be a rapid, reliable and valuable tool for the easy following of synthetic procedures for the preparation of new dyes. Thus, the synthesis of some bifunctional reactive triazine dyes has been monitored by TLC. The synthetic pathways a and b are shown in Fig. 3.12. The purity of intermediates was controlled by TLC using a silica stationary phase (Rp value of 2-allylamino-4,6-chloro-l,3,5-triazine = 0.48... 

Bis(alkylamino)-6-chloro-l,3,5-triazines are important herbicides which undergo dealkylation as the major detoxication process in animals. In vitro studies have shown that thermal dealkylation occurs via a Chugaev-like mechanism (equation 15). The dealkylation is also effected by sonication (irradiation with ultrasonic waves), but the mechanism has not been elucidated (71MI22000, 77JCS(P1)1257). It is also possible to dealkylate such 1,3,5-triazines by using hydroxyl radicals (71MI22001). 

The chloro-l,3,5-triazines have potential in chromatography. 2,4-Dichloro-6-methoxy-... 

The selectivity of the 1,3,5-triazines towards plants is primarily determined by the pathway and the rate of detoxication of these compounds in a given plant. Non-enzymatic hydrolysis of chloro-l,3,5-triazines is catalyzed by cyclic hydroxamates such as 2,4-dihydroxy-7-methoxy-l,4-benzooxazin-3(2//)-one, but the degree of tolerance to the triazines does not coincide with the content of these compounds. The chloro-l,3,5-triazines can be completely... 

When hydrogen chloride was introduced into a solution of the potassium salt of (27) in dry acetone, and the resulting precipitate treated with water, 2,4-diamino-6-chloro-l,3,5-triazine (32) was isolated. Compound (28) decomposed to melamine (33), ammonia, nitrogen and carbon dioxide when heated in dilute mineral acid, and the same compounds were obtained from (29) in the same way (Scheme 4). 

Diaminochloro-5-triazine 6-chloro-l,3,5-triazine-2,4-diamine or 2-chloro-... 

Chemical Name 2-chloro-.V-(4,6-dichloro-l,3,5-triazin-2-yl)aniline 2,4-dichloro-6-(0-chloro-anilino)-s-triazine 4,6-dichloro-V-(2-chlorophenyl)-l,3,5-triazin-2-amine... 

Substituted 4,6-diphenyl-l,3,5-triazines 943 can be obtained in high yields by palladium(0)-catalyzed reaction of the corresponding chloro-l,3,5-triazines 942 with phenylboronic acid <1993S33>. 

Chloro-l,3,5-triazines and cyanuric chloride (2,4,6-trichloro-l,3,5-triazine) are the commonest starting materials for the synthesis of many 1,3,5-triazine derivatives.10,12,14,18,19,21 Cyanuric chloride behaves like an acid chloride the chlorine atoms can be replaced sequentially but with increasing difficulty as nucleophilic attack is progressively hindered by the presence of more electron-donating substituents. The reaction mechanism is dependent on the reaction... 

In contrast to guanidine-2-carbonitriles,395 isourea-3-carbonitriles (Ai-cyanocarbamimidates) and related compounds give good yields of chloro-l,3,5-triazines 11 in condensation reactions with (chloromethylene)iminium salts.397... 

TV,TV,7V, A -Tetraalkyl-6-chloro-l,3,5-triazine-2,4-diamines 20 have been known for almost forty years as effective herbicides. Therefore, many experiments have been carried out in order to increase their biological activity by introducing suitable substituents, some examples of such herbicides are given in the table opposite. 

Bis(2,3-Dichloropropyl 2-Chloro-3-hydroxypropyl) 6-Chloro-l,3,5-triazine-2,4-diphosphonate Single Procedure 111... 

Chloro-l,3,5-triazine-2,4-diamine is one of the products of the oxidation of Atrazine with Fenton s reagent. In this case, no hydroxylated triazines can be observed. Trace amounts of carbon dioxide are generated, blit this is assumed to arise from side-chain degradation and not ring destruction.22... 

On treatment with diluted hydrochloric acid or sulfuric acid at 40 "C, compound 1 forms amidinobiuret 4 (73%) with loss of nitrogen. When anhydrous hydrochloric acid is added to a solution of the potassium salt of 1 in anhydrous acetone and the resulting precipitate is treated with water, 6-chloro-l,3,5-triazine-2,4-diamine (5) can be obtained. Treatment of 1 with aqueous potassium hydroxide for 24 hours leads to the isolation of 2,4-diamino-l,3,5-triazin-6(l/7)-one 6 (45%). Reaction of 1 with cyanamide in aqueous potassium carbonate solution affords 2, which gives l,3,5-triazine-2,4,6-triamine (7, melamine, 88%) together with ammonia, carbon dioxide and nitrogen when heated in diluted mineral acid. Product 7 can be obtained similarly from tetrazine derivative 3.3 See also Section B.2.3 on 1,3,5-triazines. 

Butyl hydroperoxide replaces chlorine in chloro-l,3,5-triazines to give (71) and (72) <81JCS(P2)1512>. HMM undergoes an unusual acyl hydroperoxide oxidative transformation to 2,4-bis(dimethylamino)-6-[(dimethylamino)oxy]-l,3,5-triazine (73). Various peracid reagents gave acceptable yields (MCPBA/CHCb 38%) (Scheme 13) <85TL5247>. 

---