ChemicalBook CAS DataBase List Pyrimethanil

Pyrimethanil synthesis

8synthesis methods

Product Name:Pyrimethanil
CAS Number:53112-28-0
Molecular formula:C12H13N3
Molecular Weight:199.25

Pyrimethanil is produced by reaction of 2-bromo-4,6-dimethylpyrimidine with aniline.

420-04-2 Synthesis

420-04-2
351 suppliers
$15.00/25g

62-53-3 Synthesis

62-53-3
658 suppliers
$10.00/1g

123-54-6 Synthesis

123-54-6
575 suppliers
$10.00/25ml

53112-28-0
230 suppliers
$45.00/500mg

Yield:53112-28-0 81.3%

Reaction Conditions:

Stage #1: CYANAMID;anilinewith hydrogenchloride in water at 45 - 90; pH=2.5; for 2 h;Inert atmosphere;
Stage #2: acetylacetonewith sodium hydroxide in water; pH=7.9; for 1 h;

Steps:

A nitrogen-inertized flange reactor was initially charged with aniline and 50% cyanamide solution in water. Subsequently, 32% hydrochloric acid was metered in up to a pH of 2.5. After the metered addition of HCl, the mixture was heated from internal temperature 45° C. to 95° C. within two hours. During the heating phase the pH was kept at 2.5 by adding further hydrochloric acid. Subsequently, acetylacetone was pumped in at internal temperature 80° C., and 50% sodium hydroxide solution was metered in up to a pH of 7.9. After a continued stirring period of one hour, the lower aqueous phase was removed. The acetylacetone excess of the upper phase was distilled off at a pressure of 750-35 mbar up to a maximum bottom temperature of 125° C. The acetylacetone distilled off can be used in subsequent batches.The bottoms were cooled to 80° C. and admixed with isopropanol. This was followed by cooling gradually to internal temperature of 0° C., and filtration of the product slurry with suction through a glass filter crucible. The reactor was rinsed through with water, which was filtered with suction. The product was washed twice with isopropanol and dried in a vacuum drying cabinet at 70° C. and 10 mbar.The isolated yield was 324 g=1.626 mol=81.3% of theory at a product purity of 97.6% (HPLC with internal standard*)) or 99.9% (GC area %**)). **) GC: 30 m DB 1701* 0.32 mm, film thickness 0.25 μm, injector 250° C., detector (FID) 300° C., injection volume 0.2 μl (0.1 g/liter of methanol), program: 50° C. (2 min), 10° C./min to 250° C. (8 min).*) HPLC: 1100 series from Agilent; Nucleosil column 120-5 C18 250×4 mm; instrument parameters: injection volume 5 μl, flow rate 1 ml/min, temperature RT, column pressure 90 bar, detector wavelength 268 nm, chromatography time 8 min; mobile phase: 250 ml of Millipore water, 750 ml of acetonitrile, 1 g of ammonium acetate; sample preparation phase: 250 ml of Millipore water, 750 ml of acetonitrile; pyrimethanil standard with known content.

References:

US2011/137033,2011,A1 Location in patent:Page/Page column 2