2-Amino-4-methoxy-6-methyl-1,3,5-triazine
English Synonyms: cv399; 2-AMINO-4-METHOXY-6-METHYL-1,3,5-TRIAZIN; 2-Amino-4-methyl-6-methoxy-s-triazine; , 3,5-triazin-2-amine; CGA-150829; 2-Methoxy-4-methyl-1,3,5-triazine- -2-amine; 4-Methyl-6-methoxy-2-amino-1,3,5-triazine
CAS number: 1668-54-8
Molecular formula: C5H8N4O
Molecular weight: 140.14
EINECS No. 216-790-7
Related classes: Amines; Building Blocks; Heterocyclic Building Blocks; Triazines; herbicide intermediate; sulfonylurea herbicides; Pesticide intermediates; triazine; heterocyclyl block; organic block; pharmaceutical raw materials; organic materials
Mol file: 1668-54-8.mol
2-Amino-4-methyl-6-methoxy-1,3,5-triazine
2-Amino-4-methyl-6-methoxy-1,3,5-triazine
Melting point 258-261 ° C (lit.)
Boiling point 114 ℃
CAS Database 1668-54-8 (CAS DataBase Reference)
EPA chemical information 1,3,5-Triazin-2-amine, 4-methoxy-6-methyl- (1668-54-8)
2-Amino-4-methyl-6-methoxy-1,3,5-triazine Usage and synthesis method
Chemical properties of colorless crystals.
Use Mainly used in paper coatings, polymer emulsion, metal processing liquid sterilization and so on
Use pesticide intermediates.
Use 2-amino-4-methoxy-6-methyl-1,3,5-triazine is the sulfonylurea herbicide metsulfuron-methyl, tribenuron-methyl, triasulfuron and other intermediate Body, can also be used for paper coatings, polymer emulsion, metal processing solution sterilization.
Production method first by the preparation of dicyano O-methyl-3-carbamidine isosuccinate hydrochloride, the latter with acetyl chloride ring reaction to generate 2-amino-4-methoxy-6-methyl-1,3 , 5-triazine.
Production methods 2-amino-4-methoxy-6-methyl-1,3,5-triazine Preparation There are two main methods.
(1) acetyl chloride method
Amidino-O-methylisourea hydrochloride is reacted with acetyl chloride.
There are two ways to synthesize amidino-O-methylisourea hydrochloride.
CuCl2 method is generally better than ZnCl2 method.
Chlorination process of the copper is added to the reaction kettle copper chloride and methanol containing two crystal water, stirred and dissolved, and then dicyandiamide is added at room temperature, heated under reflux for 3 ~ 4 h, the reaction solution was from blue Pink becomes colorless, cooling, filtration, the filter cake is copper salt complexes.
The copper salt complex was added with water and the hydrogen sulphide gas was bubbled into the reaction kettle at room temperature until the reaction mixture became black. The resulting mixture was filtered and the copper sulphide was filtered off. The filtrate was concentrated to dryness in another autoclave under reduced pressure , To obtain amidino-O-methylisourea hydrochloride, and then adding acetone to the above reaction kettle, cooling to 5 ° C, adding 20% ??sodium hydroxide under stirring, adding acetyl chloride at 0 to 5 ° C The reaction solution pH = 7, the reaction was maintained at this temperature for 2h, and then heated to room temperature for 4h, the acetone was distilled off, the residue was filtered and dried to give the product.
Process zinc chloride is added to the aqueous zinc chloride and crystallized in methanol reactor, dicyandiamide is added with stirring, heated at reflux for 4 h, cooled and filtered to give zinc complex was added to another reaction vessel zinc Salt mixture, water, heating and stirring at reflux for 40 min, filtered to remove the zinc hydroxide, the filtrate was concentrated to a syrup under reduced pressure, was added anhydrous ethanol to remove a small amount of unhydrolyzed zinc salt complex, part of the ethanol was evaporated and cooled to give crystalline amidino -O- methylisourea hydrochloride, the salt was dispersed in a solution of acetonitrile and sodium hydroxide, stirred at 0 ° C was added dropwise acetyl chloride, and then added at room temperature for 3 h, the vacuum was distilled off large Part of the solvent, add water cooling filter, dried to obtain a white crystal product.
(2) trimethyl orthoacetate method
By acetonitrile and methanol in the presence of hydrogen chloride to generate trimethyl orthoacetate, trimethyl orthoacetate and dicyandiamide in the presence of zinc chloride prepared triazine.
The process is added acetonitrile and methanol in an autoclave, kept at 5 ℃, Walter dry hydrogen chloride gas, 15 h reaction at 20 ℃, with 5% ammonia methanol solution to adjust pH = 3, then methanol was added, at 30 deg.] C The reaction 15 h, filtered to remove ammonium chloride, atmospheric distillation, collecting. 107 ~ 109 ℃ fraction of trimethyl orthoacetate.
In another reaction vessel were added dicyandiamide, zinc chloride and trimethyl orthoacetate was stirred and heated to 75 ~ 85 ℃, the reaction for 16 h, methanol was distilled off under reduced pressure and the excess trimethyl orthoacetate, water was added, the crystalline Filter and dry to give triazine.