Hydrazine, 1,1-diphenyl-, hydrochloride (1:1) → HCID 22105111, Verbindung

HRID 476410

Reaktionsgleichung

Reaktionsgleichung von HRID 476410
[CH2:1]1[CH2:8][C:6](=O)[C:4](=O)[CH2:3][CH2:2]1.Cl.[C:10]1([N:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)N)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)(=O)C>[C:6]1([N:16]2[C:18]3[C:23](=[CH:22][CH:21]=[C:20]4[C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=5[N:16]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)[C:19]4=3)[C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:4]=[CH:3][CH:2]=[CH:1][CH:8]=1

Komponenten

4

Edukt 2

HCID 10738Hydrazine, 1,1-diphenyl-, hydrochloride (1:1)HCID 130061,2-Cyclohexanedione

Produkt 1

HCID 22105111HCID 22105111, VerbindungAusbeute 57,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

1,2-Cyclohexadione (98%; 5.0 g, 1 eq.) is dissolved in acetic acid (100%; 30 ml). 1,1-Diphenylhydrazine hydrochloride (98%; 19.68 g, 2 eq.) is slowly added thereto. The suspension is stirred at room temperature overnight. Subsequently, the reaction is stirred at reflux for 54 h. After cooling to room temperature, the suspension is filtered with suction and washed with a little acetic acid. The residue is suspended in hot distilled water, filtered off with suction and washed to neutrality. The solid is dried under reduced pressure overnight. Subsequently, the solid is dissolved in toluene (300 ml) and Pd/C (10%; 2 g) is added; the mixture is stirred at reflux overnight. The solution was filtered through Celite (super standard) and washed with toluene and methylene chloride. The clear solution is concentrated and the residue is dried at 100° C. under reduced pressure. This gives 5.11 g of compound 4, 57.2% yield.

Aufarbeitung

  1. stirringSubsequently, the reaction is stirred
  2. temperatureat reflux for 54 h
  3. temperatureAfter cooling to room temperature
  4. filtrationthe suspension is filtered with suction
  5. washwashed with a little acetic acid
  6. distillationin hot distilled water
  7. filtrationfiltered off with suction
  8. washwashed to neutrality
  9. customThe solid is dried under reduced pressure overnight
  10. dissolutionSubsequently, the solid is dissolved in toluene (300 ml)
  11. additionPd/C (10%; 2 g) is added
  12. stirringthe mixture is stirred
  13. temperatureat reflux overnight
  14. filtrationThe solution was filtered through Celite (super standard)
  15. washwashed with toluene and methylene chloride
  16. concentrationThe clear solution is concentrated
  17. customthe residue is dried at 100° C. under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-801948ef2fba41688a0b9b65b6eed340
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637857B2

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