Hydrochloric Acid → HCID 178469357, compound

HRID 2194694Notes

Reaction equation

Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[NH:10][NH2:11].C(=O)([O-])[O-].[K+].[K+].[C:18](OCC)(=[O:26])[C:19]#[C:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].Cl>C(O)C>[F:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[N:10]1[C:18]([OH:26])=[CH:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:11]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2,5-difluorophenyl)hydrazine hydrochloride (25.0 g) in ethanol (500 mL) were added potassium carbonate (38.3 g) and diethyl but-2-ynedioate (23.6 g). After refluxing for 18 hr, the mixture was cooled to 0° C. and acidified with 6 mol/L hydrochloric acid. Ethanol was evaporated under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with a mixed solvent of ethyl acetate and diisopropyl ether, and the obtained solid was collected by filtration and dried under reduced pressure to give the title compound as a pale-yellow solid (yield 22.7 g, yield 61%).

Workup

temperatureAfter refluxing for 18 hr
customEthanol was evaporated under reduced pressure
extractionthe residue was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
washThe residue was washed with a mixed solvent of ethyl acetate and diisopropyl ether
filtrationthe obtained solid was collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-6dba9c9dc3fd4acf90dce4a05a2442dc
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334301B2

Reaction notes

Loading…