Naproanilide

Naproanilide is a member of naphthalenes.

Preparation method 1: Preparation of α-bromopropionyl anilide 12.3g of phosphorus oxychloride was gradually added dropwise to 36.7g (0.24mol) of α-bromopropionic acid under stirring, and the temperature was controlled to be below 40°C. 18.6g (0.2mol) of aniline was gradually added dropwise, the temperature was raised, and the reaction was stirred at 110-120°C for 1.5h. Cool to 80°C and add a small amount of water. Suction filtration, washing with water, and drying at 50-60°C to obtain 54.4-58 g of crude product. After recrystallization and decolorization, 40.1-41.3g of pure product is obtained. m.p. 96～97.5℃, the yield is 88%～90%. Preparation of naprolamine 8.9g β-naphthoic acid (0.06mol) and 24g 10% NaOH (0.06mol) are heated and dissolved. In addition, 0.4g of triethylbenzylammonium chloride for indication phase transfer catalyst is added. In addition, 11.4g (0.05mol) of α-bromopropionylanilide was dissolved in 100 mL of benzene and added dropwise to β-naphthol sodium hydroxide solution. At the same time, it is heated in a water bath, and the addition is completed within 1.5 to 2 hours at a bath temperature of 60 to 70°C, and the reaction is kept for 4 hours. Cool, separate layers, extract the water layer with benzene, and merge the oil layers. After removing benzene under normal pressure, 16～17.5g of crude product is obtained after cooling, and 10.5～10.9g of pure product is obtained after recrystallization. The melting point is 127～128℃, and the yield is 72.1%～74.9%. Can also use phosgene instead of POCl3 preparation. Firstly, phosgene and α-chloropropionic acid are reacted to generate acid chloride; the acid chloride is treated with aniline to generate α-chloropropionanilide; the gaseous by-products are removed, β-naphthol is added, and the reaction is completed and cooled, and the product is precipitated in crystal form . Advantages of this method: all by-products are gases, simplifying the operation; using toluene as the solvent, the second and third steps are combined into one step without filtering the intermediate products; using toluene as a solvent can effectively prevent α-chlorine The decomposition of propionic acid improves the utilization of raw materials. Preparation method Two α-chloropropionic acid reacts with β-naphthol to generate 2-(2-naphthyloxy) propionic acid, which is then chlorinated with phosgene or PCl3 to generate α-(2-naphthyloxy) propionyl chloride. Finally, it reacts with aniline to obtain naprotamine.

This product has a contact effect on perennial and annual weeds, such as melon fur, cattle felt, sedge grass and so on. Has a special effect on melon fur.

Molecular Weight:291.3
XLogP3:4.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:291.125928785
Monoisotopic Mass:291.125928785
Topological Polar Surface Area:38.3
Heavy Atom Count:22
Complexity:364
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes