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

HRID 353210Notes

Reaction equation

HRID 353210 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

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 78373Dimethylformamide dimethyl acetalHCID 227080301-(2-Furyl)-2-pyridin-4-ylethanone

Product 1

HCID 670738543-(Dimethylamino)-1-(furan-2-yl)-2-(pyridin-4-yl)prop-2-en-1-oneYield 97%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

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

Workup

  1. temperatureAfter cooling as it
  2. extractionThe aqueous layer was extracted with ethyl acetate (×6)
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5151ff71f75145c1a14c2ea474a15365
Source dataset
uspto-grants-2004_06
Patent number
US06750232B2

Reaction notes

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