Triethylamine → HCID 131729878, compound

2 g (10.1 mmol) of 2,4-dichlorphenylacetic acid were initially charged in 50 ml of dichloromethane, 1.1 ml (1.67 eq) of oxalyl chloride and a drop of DMF were added and the mixture was heated at the boil under reflux until the evolution of gas had ceased. The mixture was concentrated under reduced pressure, and two more times, dichloromethane was added and the mixture was concentrated again, and the residue was then taken up in 5 ml of dichloromethane. The solution obtained in this manner was, at 0° C., added dropwise over a period of 20 min to a solution of 1.4 g (1.1 eq) of methyl 2-(methylhydrazono)propionate and 2.9 ml of triethylamine (2.1 eq) in 20 ml of dichloromethane. The mixture was then stirred at room temperature overnight, and 30 ml of water were added. The aqueous phase was removed and the organic phase was concentrated. The residue obtained was purified by column chromatography (silica gel, gradient n-heptane/ethyl acetate). This gave a total of 0.7 g of methyl 2-{[2-(2,4-dichlorophenyl)acetyl]methyl-hydrazono}propionate.

1. temperaturethe mixture was heated at the boil
2. temperatureunder reflux until the evolution of gas
3. concentrationThe mixture was concentrated under reduced pressure, and two more times, dichloromethane
4. additionwas added
5. concentrationthe mixture was concentrated again
6. customThe solution obtained in this manner
7. customwas, at 0° C.
8. customThe aqueous phase was removed
9. concentrationthe organic phase was concentrated
10. customThe residue obtained
11. customwas purified by column chromatography (silica gel, gradient n-heptane/ethyl acetate)

ORD record

ord-83dd2c6bbf2b446d94ace7f63b0e8ea1

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242055B2