Ammonium Chloride → 3-(Dimethylamino)-1-(furan-2-yl)-2-(pyridin-4-yl)prop-2-en-1-one

HRID 747142Notes

Reaction equation

CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](=[O:22])[CH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.[Cl-].[NH4+]>C(OCC)(=O)C>[CH3:6][N:4]([CH3:5])[CH:3]=[C:15]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[C:14]([C:10]1[O:9][CH:13]=[CH:12][CH:11]=1)=[O:22]

Participants

Conditions

Temperature: 100 °C

Procedure

N,N-Dimethylformamide dimethyl acetal (5 ml) was added to 1-(2-furyl)-2-(4-pyridyl)-1-ethanone (2.0 g, 10.7 mmol) and the mixture was stirred at 100° C. for 2 hours. After cooling as it was, the reaction mixture was diluted with ethyl acetate and a saturated aqueous ammonium chloride solution. The aqueous layer was extracted with ethyl acetate (×6). The combined organic layers were dried over anhydrous sodium sulfate and then concentrated, to give the title compound (2.5 g, 97%) as a reddish brown oil.

Workup

temperatureAfter cooling as it
extractionThe aqueous layer was extracted with ethyl acetate (×6)
dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-42d58e758edb4d8c8e736afe3be9e600
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396836B2

Reaction notes

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