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Methane → HCID 178448403, Verbindung

HRID 2250388
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2250388
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:9][CH:10]([CH2:14][CH3:15])[C:11](O)=O.C>O>[Cl:9][CH:10]([C:11]1[NH:1][C:2]2=[N:3][CH:4]=[CH:5][CH:6]=[C:7]2[N:8]=1)[CH2:14][CH3:15]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 297MethaneHCID 99562,3-DiaminopyridineHCID 201372-Chlorobutyric acid

Produkt 1

HCID 178448403HCID 178448403, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5.0 g of 2,3-diaminopyridine in 200 g of polyphosphoric acid are heated at 120° C. for 0.5 h. The solution is cooled to 80° C. and 5.7 ml of 2-chlorobutyric acid are added. Thereafter, the reaction mixture is heated to 130° C. for 22 h. After cooling, the polyphosphoric acid is hydrolysed with 136 ml of water. After reheating to 90° C., charcoal is added under vigorous stirring. Subsequently, the suspension is filtered through a celite pad while still hot (70° C.). The filter cake is rinsed with 100 ml of water and the pH 4 using 9 M aqueous sodium hydroxide solution. The mixture is extracted three times each with 200 ml of ethyl acetate, the combined organic phases are dried using sodium sulfate, concentrated and purified by chromatography on silica gel (eluent: toluene/ethyl acetate 1:1) to give 5.19 g of the title compound as a colorless, amorphous solid. M.p. 137° C. MS: 196.0/198.0 (MH+, 100%/32%). TLC: Rf=0.50 (dichloromethane/methanol 10:1).

Aufarbeitung

  1. temperatureThereafter, the reaction mixture is heated to 130° C. for 22 h
  2. temperatureAfter cooling
  3. customAfter reheating to 90° C.
  4. filtrationSubsequently, the suspension is filtered through a celite pad while still hot (70° C.)
  5. washThe filter cake is rinsed with 100 ml of water
  6. extractionThe mixture is extracted three times each with 200 ml of ethyl acetate
  7. customthe combined organic phases are dried
  8. concentrationconcentrated
  9. custompurified by chromatography on silica gel (eluent: toluene/ethyl acetate 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-18bc8f655b7a45e29587cb2b09ae389a
Quelldatensatz
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07317021B2

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