Preparation and application of 2,6-dichloropyridine-4-methylamine_Industrial additives

Preparation and application background and overview of 2,6-dichloropyridine-4-methylamine

2,6-Dichloropyridine-4-methylamine can be used as a pharmaceutical synthesis intermediate. It can be prepared from 4-(hydroxymethyl)-2,6-dichloropyridine as the reaction raw material and can be used to prepare sulfonamides. Compounds with significant agricultural and horticultural insecticidal, acaricidal, nematocidal and fungicidal activities.

Preparation and application of 2,6-dichloropyridine-4-methylamine

1) Add 0.95g 4-(hydroxymethyl)-2,6-dichloropyridine and 326mg sodium azide to 5.00mL of N,N-dimethylformamide, and heat the mixture at 70°C Stir down. The reaction solution was concentrated, water was added to the residue, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, the sodium sulfate was filtered off, and the organic layer was concentrated to obtain 810 mg of azide.

2) Add 1.35g of phenanthreneboric acid azide obtained in the above step and 1.94g of triphenylphosphine to 30.00mL of tetrahydrofuran and 3.00mL of water, and stir the mixture at room temperature overnight. The reaction solution was concentrated, and the residue was purified by silica gel flash chromatography (eluting with methanol-chloroform) using a fast automatic purifier (Biotage AB/Isolera TM) to obtain 220 mg of 2,6-dichloropyridine-4-methyl. Aminomethylamine compounds.

Preparation and application of 2,6-dichloropyridine-4-methylamine

2,6-Dichloropyridine-4-methylamine can be used to prepare sulfonamide compounds, which have significant agricultural and horticultural insecticidal, acaricidal, nematicidal and bactericidal activities. The specific reaction steps are: convert 2,6 -Dichloropyridine-4-methylamine compound and 40.30mL triethylamine were added to 530mL methylene chloride, and the solution was cooled to 0°C. After cooling, 83.80g of 4-iodobenzenesulfonyl chloride was added in several portions. solution, and the mixture was stirred at room temperature for 2.5 hours. Water was added to the reaction solution, and the white solid was filtered. The solid was washed twice with water and once with dichloromethane, and dried under reduced pressure to obtain 99.72 g of a sulfonamide compound.

References

[1] WO2014065411 – SULFONAMIDE DERIVATIVE AS HARMFUL-ORGANISM CONTROL AGZirconium Carbonate ENT FOR AGRICULTURAL/HORTICULTURAL USE