Hydrochloric Acid → HCID 54348027, compound

Separately, a 100-mL three-necked flask equipped with a thermometer, a dropping funnel, a three-way stopcock, and a magnetic stirrer was purged with nitrogen. Thereto, were added 10.2 g (52.2 mmol) of 2,6-dichlorobenzyl chloride (produced by Tokyo Kasei K.K.), and 25 mL of tetrahydrofuran. To this solution, the above obtained solution of the lithium salt compound was added dropwise by keeping the temperature of the reaction system in the range from 15 to 20° C. The reaction mixture was aged at room temperature for 2 hours, and the cooled with ice. Thereto 3N hydrochloric acid solution was added to stop the reaction. The mixture was extracted with ether. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. To the flask containing the concentration residue, 10 g of Molecular Sieve 4A was added and the flask was purged with nitrogen. The concentration residue was dissolved by addition of 10 mL of toluene, and was cooled with ice. Thereto, 3.45 g (57.4 mmol) of N,N-dimethylhydrazine was added. The mixture was stirred at room temperature for 3 hours, and filtered. The filtrate was concentrated under a reduced pressure. The obtained concentration residue was purified by silica gel chromatography (Solvent: hexane, ratio of hexane:ethyl acetate=20:1) to obtain 7.42 g (30.3 mmol) of 3-(2,6-dichlorophenyl)propionaldehyde N,N-dimethylhydrazone. (Yield: 58% based on 2,6-dichlorobenzyl chloride).

1. customSeparately, a 100-mL three-necked flask equipped with a thermometer, a dropping funnel
2. customa three-way stopcock, and a magnetic stirrer was purged with nitrogen
3. customfrom 15 to 20° C
4. temperaturethe cooled with ice
5. customthe reaction
6. extractionThe mixture was extracted with ether
7. dry with materialThe organic phase was dried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. additionTo the flask containing the concentration residue, 10 g of Molecular Sieve 4A
11. additionwas added
12. customthe flask was purged with nitrogen
13. dissolutionThe concentration residue was dissolved by addition of 10 mL of toluene
14. temperaturewas cooled with ice
15. filtrationfiltered
16. concentrationThe filtrate was concentrated under a reduced pressure
17. concentrationThe obtained concentration residue
18. customwas purified by silica gel chromatography (Solvent: hexane, ratio of hexane:ethyl acetate=20:1)

ORD record

ord-c8fd9eb046164c44ac3b4470b74d2d4c

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06346621B1