Pyridine → N-(3,5-Dinitrophenyl) nonanamide

HRID 978101

Reaktionsgleichung

Reaktionsgleichung von HRID 978101
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[NH2:7])([O-:3])=[O:2].N1C=CC=CC=1.[C:20](Cl)(=[O:29])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>ClC(Cl)C>[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][C:20](=[O:29])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 120683,5-DinitroanilineHCID 69819Nonanoyl chloride

Produkt 1

HCID 13825720N-(3,5-Dinitrophenyl) nonanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

3,5-Dinitroaniline, 10.0 g (0.055 mole), is dissolved in 200 ml dichloroethane, containing 25 ml pyridine. The solution is stirred at room temperature while nonanoyl chloride, 10.3 g (0.058 mole), is added slowly. The solution is stirred for 2 hours. Excess pyridine is removed by washing the product with 4N hydrochloric acid. The product is obtained by crystallization at -20° C. and recrystallized from 95% ethanol. There is obtained N-(3,5-Dinitrophenyl) nonanamide (M.P. 72.5°-73.0° C.). Analysis shows 12.69% nitrogen as against a calculated value of 12.61% for C15H21N3O5.

Aufarbeitung

  1. additionis added slowly
  2. customExcess pyridine is removed
  3. washby washing the product with 4N hydrochloric acid
  4. customThe product is obtained by crystallization at -20° C.
  5. customrecrystallized from 95% ethanol

Quellen und Nachweise

ORD-Eintrag
ord-61dcfb17a5c740bab1848da503670eae
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04663353

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