2-Amino-4-methoxy-6-methyl-1,3,5-triazine

DryPowder

2-methyl-4-amino-6-methoxy-s-triazine is a monoamino-1,3,5-triazine that is 1,3,5-triazin-2-amine substituted by a methoxy group at position 4 and a methyl group at position 6. It is a metabolite of the herbicide thifensulfuron-methyl. It has a role as a marine xenobiotic metabolite. It is a monoamino-1,3,5-triazine and an aromatic ether.

The preparation of 2-amino-4-methoxy-6-methyl-1, 3, 5-triazine mainly has the following two methods. (1) Acetyl chloride famidinyl-O-methylisourea hydrochloride reacts with acetyl chloride. There are two methods for the synthesis of amidino-O-methylisourea hydrochloride. Generally, the CuCl2 method is better than the ZnCl2 method. The process of the copper chloride method is to add copper chloride and methanol containing two crystal waters into the reaction kettle, stir to dissolve, and then add dicyandiamide at room temperature, and heat to reflux for 3 to 4 hours. The pink color becomes colorless, cooled, filtered, and the filter cake is the copper salt complex. Add the copper salt complex and water together in the reaction kettle, add hydrogen sulfide gas at room temperature while stirring, until the reaction mixture turns black, filter to filter out copper sulfide, and concentrate the filtrate in another reaction kettle under reduced pressure to dryness , To obtain amidino-O-methyl isourea hydrochloride, then, add acetone to the above reaction kettle, cool to 5 ℃, add 20% sodium hydroxide while stirring, add acetyl chloride at 0-5 ℃ to make The pH of the reaction solution was 7, and the reaction was maintained at this temperature for 2 hours, and then raised to room temperature for 4 hours. The acetone was distilled off, and water was added to the residue to filter and dry to obtain the product. The process of the zinc chloride method is to add the hydrous crystals zinc chloride and methanol into the reactor, add dicyandiamide under stirring, heat to reflux for 4 h, cool and filter to obtain the zinc salt complex, add zinc to another reactor The salt mixture and water are heated and stirred to reflux for 40 min. The zinc hydroxide is removed by filtration. The filtrate is concentrated under reduced pressure to a slurry state. Anhydrous ethanol is added to remove a small amount of unhydrolyzed zinc salt complexes. Part of the ethanol is evaporated and cooled to obtain crystalline amidine groups. -O-Methyl isourea hydrochloride, disperse the salt in a solution of acetonitrile and sodium hydroxide, stir and add acetyl chloride dropwise at 0°C. After the addition, stir at room temperature for 3 h. Part of the solvent is added with water, cooled and filtered, and dried to obtain a white crystal product. (2) The trimethyl orthoacetate method generates trimethyl orthoacetate by reacting acetonitrile and methanol in the presence of hydrogen chloride, and the trimethyl orthoacetate reacts with dicyandiamide in the presence of zinc chloride to prepare triazine. The process is to add acetonitrile and methanol into the reactor, keep it at 5℃, pass dry hydrogen chloride gas, react at 20℃ for 15 hours, adjust pH=3 with 5% ammonia methanol solution, and then add methanol at 30℃ React for 15 h, filter to remove ammonium chloride, distill under normal pressure, and collect. The distillate at 107～109℃ is trimethyl orthoacetate. Add dicyandiamide, zinc chloride and trimethyl orthoacetate into another reaction kettle, stir and heat to 75～85℃, react for 16h, distill off methanol and excess trimethyl orthoacetate under reduced pressure, add water to crystallize Filter and dry to obtain triazine.

2-Amino-4-methoxy-6-methyl-1,3,5-triazine is an intermediate of sulfonylurea herbicides methylsulfuron, chlorsulfuron, thifensulfuron-methyl, bensulfuron-methyl, etc. It can also be used for sterilization and anticorrosion of paper-making coatings, polymer emulsions and metal working fluids.

Intermediates

Molecular Weight:140.14
XLogP3:0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:140.06981089
Monoisotopic Mass:140.06981089
Topological Polar Surface Area:73.9
Heavy Atom Count:10
Complexity:110
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes