2.4.6- Trichloro triazine catalyst

Organic Derivatives. Although numerous mono-, di-, and trisubstituted organic derivatives of cyanuric and isocyanuric acids appear in the hterature, many are not accessible via cyanuric acid. Cyanuric chloride 2,4,6-trichloro-j -triazine [108-77-0], is generally employed as the intermediate to most cyanurates. Trisubstituted isocyanurates can also be produced by trimerization of either aUphatic or aromatic isocyanates with appropriate catalysts (46) (see Isocyanates, organic). Alkylation of CA generally produces trisubstituted isocyanurates even when a deUberate attempt is made to produce mono- or disubstituted derivatives. There are exceptions, as in the production of mono-2-aminoethyl isocyanurate [18503-66-7] in nearly quantitative yield by reaction of CA and azitidine in DMF (47). 

Synthesis of 1,3,5-triazine cannot be achieved by catalytic hydrogenation of cyanuric chloride (2,4,6-trichloro-l,3,5-triazine), probably due to poisoning of the catalyst by 1,3,5-triazine.36,37 When one, two or all of the chlorine atoms of cyanuric chloride are replaced by amino, methoxy, methylsulfanyl or alkyl groups, reduction with hydrogen iodide and phospho-nium iodide, sodium in liquid ammonia, or catalytic hydrogenation, e.g. to give 1, can be accomplished.38-46 Reduction with zinc in acetic acid could not be achieved.44. 

Cyanuric chloride (2,4,6-trichloro-l,3,5-triazine) resembles the nitrogen analog of an acid chloride (imidoyl chloride). The chlorine atoms can be replaced sequentially using different reaction conditions. The rate of reaction for such processes which involve cyanuric chloride or other chlorotriazines is dependent on solubility, temperature, actual ring substitution, the catalyst used and the nature of the nucleophile. Several reviews on the chemistry of cyanuric chloride reactions are reported.54 66... 

Cyanuric chloride (2,4,6-trichloro-l,3,5-triazine), mp 145" C, bp 190°C, is produced commercially by gaseous trimerization of cyanogen chloride over charcoal catalysts. Cyanuric chloride behaves as a heterocyclic acid chloride analogue. Its reactive chlorine atoms are easily substituted (also stepwise) by S]sjAr processes ... 

All condensation steps can be facilitated by the addition of a Brpnsted or Lewis acid, which increases the reaction rate. Thus, various catalyst systems have been examined and proven as applicable. Among them are simple proton sources like montmorillonite K-10 (MK-10) [218], cellulose [219], silica [220], sulfuric acid, or several Lewis acids [221]. Also, in situ generated HCl, from 2,4,6-trichloro[l,3,5]triazine (TCT) [222], and materials... 

A good number of alternative methods are also available in literature for the synthesis of 1,5-benzodiazepine derivatives involving the use of a variety of catalysts such magnesium oxide/ phosphorus oxychloride (MOPO) [1], ionic liquid (1,3-di-n-butylimidazolium bromide) [2], silica gel-supported cerium(lll) chloride/sodium iodide [3], Sc(OTf)3 [4], InCls [5], InBr3 [6], ceric ammonium nitrate (CAN) [7], 2,4,6-trichloro-l,3,5-triazine (TCT) [8,9], GaCl3 [10], and Zr0C2-8H20 [11] in the presence or absence of solvent(s) at room temperature. 

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