Hydrazine, propyl- → HCID 54358958, Verbindung

HRID 1447801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1447801
[C:1]1([CH:7]=[C:8]2[C:13](=O)[C:12](=[CH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][O:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:22]([NH:25][NH2:26])[CH2:23][CH3:24]>CO>[C:1]1([C:7]2[N:25]([CH2:22][CH2:23][CH3:24])[N:26]=[C:13]3[C:12](=[CH:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:11][O:10][CH2:9][C:8]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 42007Hydrazine, propyl-HCID 286335tetrahydro-3,5-bis(phenylmethylene)-4H-pyran-4-one

Produkt 1

HCID 54358958HCID 54358958, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of tetrahydro-3,5-bis-(phenylmethylene)-4H-pyran-4-one (3.6 g, 13 mmole) and propylhydrazine (1.1 g, 14 mmole) in methanol (250 ml) is heated at reflux temperature for 3-4 hours. MeOH is then removed in vacuo. The residue is dissolved in CHCl3 and washed with dilute HCl and water, then dried (anhydrous MgSO4) and concentrated in vacuo to give a yellow oil. When this crude oil is triturated with a small amount of acetonitrile the major product of this reaction precipitates out. The filtrate is concentrated and the residue is applied to a dry-packed Al2O3 (Activity I, neutral) column. The fractions eluted with ether are combined and recrystallized first from ether/hexane, then from cyclohexane until a constant m.p. (126.5°-128.5° C.) is reached, giving the product in crystalline form (99% pure).

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux temperature for 3-4 hours
  3. customMeOH is then removed in vacuo
  4. dissolutionThe residue is dissolved in CHCl3
  5. washwashed with dilute HCl and water
  6. dry with materialdried (anhydrous MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a yellow oil
  9. customWhen this crude oil is triturated with a small amount of acetonitrile the major product of this reaction
  10. customprecipitates out
  11. concentrationThe filtrate is concentrated
  12. washThe fractions eluted with ether
  13. customrecrystallized first from ether/hexane
  14. customuntil a constant m.p. (126.5°-128.5° C.)
  15. customgiving the product in crystalline form (99% pure)

Quellen und Nachweise

ORD-Eintrag
ord-3d66483f2a8c4f7099abcf59fb4e065e
Quelldatensatz
uspto-grants-1979_12
Patentnummer
US04178379

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