Iodoethane → 4-Benzamido-1-ethyl-3-fluoro-pyridinium iodide

HRID 1257564Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257564
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[I:17][CH2:18][CH3:19].C(OCC)(=O)C>CN(C)C=O>[I-:17].[C:9]([NH:8][C:7]1[CH:6]=[CH:5][N+:4]([CH2:18][CH3:19])=[CH:3][C:2]=1[F:1])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 67323663N-(3-fluoropyridin-4-yl)benzamide

Produkt 1

HCID 673241664-Benzamido-1-ethyl-3-fluoro-pyridinium iodide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of N-(3-fluoro-pyridin-4-yl)-benzamide (1.95 kg, 9.0 mol) in anhydrous dimethylformamide (10 L) was placed under nitrogen atmosphere and heated at 70° C. The heated solution was charged with iodoethane via dropwise addition (1.55 kg/0.795 L, 9.9 mol) with temperature monitoring. The addition caused an exoterm that raised the internal reactor temperature to 110° C. for the duration of the addition. A temperature of 100° C. was maintained for a further two hours before the reaction was cooled to room temperature. The reaction mixture was poured into ethyl acetate (50 L, pre-cooled to 5° C.) and stirred for one hour. The precipitated solid was collected by filtration and washed with ethyl acetate (3×10 L). The yellowish solid 4-benzamido-1-ethyl-3-fluoro-pyridinium iodide was dried in a tray vacuum oven at 50° C., yielding 3.25 kg. (97%). 1H NMR (400 MHz, DMSO): δ 11.37 (1H, s), 9.41 (1H, dd, J=5.86, 1.56 Hz), 8.88 (1H, dd, J=7.03, 1.56 Hz), 8.73 (1H, t, J=7.42 Hz), 7.99 (2H, d, J=8.20 Hz), 7.72 (1H, t, J=7.42 Hz), 7.61 (2H, t, J=8.20 Hz), 4.52 (2H, q, J=7.42 Hz), 1.54 (3H, t, J=7.42 Hz).

Aufarbeitung

  1. additionThe addition
  2. temperatureraised the internal reactor temperature to 110° C.
  3. additionfor the duration of the addition
  4. temperatureA temperature of 100° C. was maintained for a further two hours before the reaction
  5. temperaturewas cooled to room temperature
  6. filtrationThe precipitated solid was collected by filtration
  7. washwashed with ethyl acetate (3×10 L)
  8. dry with materialThe yellowish solid 4-benzamido-1-ethyl-3-fluoro-pyridinium iodide was dried in a tray vacuum oven at 50° C.
  9. customyielding 3.25 kg

Quellen und Nachweise

ORD-Eintrag
ord-c6f13428ff224af49b66ac1078a86275
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461328B2

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