Water → 2-chloro-N-(1-ethyl-1H-pyrazol-5-yl)-N-isopropylacetamide

1-Ethyl-N-isopropyl-1H-pyrazol-5-amine (0.49 g, 3.2 mmol) was dissolved in dichloromethane (11 ml) and stirred in an ice bath. N,N-diisopropylethylamine (1.14 ml, 6.4 mmol) was added followed by slow addition of chloroacetyl chloride (0.51 ml, 6.4 mmol). The reaction was stirred to 25° C. over 16 h. Water (100 ml) and ethyl acetate (100 ml) were added and the phases were separated. The aqueous phase was extracted with ethyl acetate (2×50 ml) and the combined organic phases were washed with a saturated aqueous sodium chloride solution (25 ml). After drying over sodium sulfate and evaporation the residue was purified by silica gel chromatography (5-80% ethyl acetate/hexanes) to give 0.39 g (53%) of 2-chloro-N-(1-ethyl-1H-pyrazol-5-yl)-N-isopropylacetamide as a brownish solid. MS (ESI) m/z 230 [M+H]+.

1. stirringThe reaction was stirred to 25° C. over 16 h
2. customthe phases were separated
3. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
4. washthe combined organic phases were washed with a saturated aqueous sodium chloride solution (25 ml)
5. dry with materialAfter drying over sodium sulfate and evaporation the residue
6. customwas purified by silica gel chromatography (5-80% ethyl acetate/hexanes)

ORD record

ord-a5ea1a6a970940ecb2a4a82e733bafda

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09248199B2