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Such reactions rely on the easy displacement of the chloride with nucleophiles such as amines: (ClCN) 3 + 2 RNH 2 → (RNHCN)(ClCN) 2 + RNH 3 + Cl −. Other triazine herbicides, such as simazine, anilazine and cyromazine are made in an analogous way. [3] Cyanuric chloride is also used as a precursor to dyes and crosslinking agents.
With amines, one or more chloride is displaced. The remaining chlorides are reactive, and this theme is the basis of the large field of reactive dyes. Cyanuric chloride assists in the amidation of carboxylic acids. [3] The 1,2,4-triazines can react with electron-rich dienophiles in an inverse electron demand Diels-Alder reaction. This forms a ...
Beckmann reaction. The reaction mechanism for this reaction is based on a catalytic cycle with cyanuric chloride activating the hydroxyl group via a nucleophilic aromatic substitution. The reaction product is dislodged and replaced by new reactant via an intermediate Meisenheimer complex. Beckmann cyanuric acid cataly cycle
Cyanuric chloride (2,4,6-trichloro-1,3,5-triazine) is the starting point for the manufacture of many herbicides such as Simazine and atrazine. Chlorinated triazines are the basis of an important family of reactive dyes , which are covalently attached to cellulosic materials.
When using oxalyl chloride as the dehydration agent, the reaction must be kept colder than −60 °C to avoid side reactions. With cyanuric chloride [11] or trifluoroacetic anhydride [12] instead of oxalyl chloride, the reaction can be warmed to −30 °C without side reactions.
Simazine may be prepared from cyanuric chloride and a concentrated solution of ethyl amine (at least 50 percent by number) in water. [1] The reaction is highly exothermic and is therefore best carried out below 10 °C.
Reactions between aldimines and α-methylene carbonyls are also considered Mannich reactions because these imines form between amines and aldehydes. The reaction is named after Carl Mannich. [2] [3] Scheme 1 – Ammonia or an amine reacts with formaldehyde and an alpha acidic proton of a carbonyl compound to a beta amino carbonyl compound.
The name "Schotten–Baumann reaction conditions" often indicate the use of a two-phase solvent system, consisting of water and an organic solvent. The base within the water phase neutralizes the acid, generated in the reaction, while the starting materials and product remain in the organic phase, often dichloromethane or diethyl ether .