Water → 2-Hexadecylamino-5-nitropyridine

HRID 1074123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1074123
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH2:11]([NH2:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C([O-])(O)=O.[Na+].O>C(Cl)(Cl)Cl.CN(C=O)C>[CH2:11]([NH:27][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8926HexadecylamineHCID 783082-Chloro-5-nitropyridineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 221557642-Hexadecylamino-5-nitropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21754633chloroform N,N-dimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

0.5 g (3.2 mmol) of 2-chloro-5-nitropyridine (Fluka, purum), 0.76 g (3.2 mmol) of hexadecylamine (Merck-Schuchard, for synthesis) and 1 g of NaHCO3 are weighed out and suspended in 10 ml of CHCl3 /DMF 1:1 (puriss., for analysis). The suspension is heated to 100° C. (bath temperature) and stirred for 4 hours at this temperature. When the reaction mixture has cooled, water is added and extraction is carried out with diethyl ether. The organic phase is extracted twice with water and dried over Na2SO4. After evaporation of the solvent, the residue is chromatographed on 50 times the amount of silica gel (eluent=hexane/ether 95:5). The slightly yellowish product fraction is concentrated and 1 is recrystallized again from hexane/ether.

Aufarbeitung

  1. temperatureWhen the reaction mixture has cooled
  2. extractionextraction
  3. extractionThe organic phase is extracted twice with water
  4. dry with materialdried over Na2SO4
  5. customAfter evaporation of the solvent
  6. customthe residue is chromatographed on 50 times the amount of silica gel (eluent=hexane/ether 95:5)
  7. concentrationThe slightly yellowish product fraction is concentrated
  8. custom1 is recrystallized again from hexane/ether

Quellen und Nachweise

ORD-Eintrag
ord-c314f438f6134fd9930e87a1cbeaee9e
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04973429

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