Methylhydrazine → 1-Methyl-4-(4-methylphenyl)-1H-pyrazole

HRID 1635840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1635840
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:11]=O)[CH:9]=O)=[CH:4][CH:3]=1.[CH3:13][NH:14][NH2:15]>C(O)C>[CH3:13][N:14]1[CH:11]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:9]=[N:15]1

Komponenten

4

Edukt 2

HCID 6061MethylhydrazineHCID 27369302-(4-Methylphenyl)malondialdehyde

Produkt 1

HCID 43190701-Methyl-4-(4-methylphenyl)-1H-pyrazoleAusbeute 89,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-methylphenyl)-malondialdehyde (3.05 g), absolute ethanol (40 ml), and methylhydrazine (1.09 g) was stirred at room temperature for 18 hours and the volatiles removed at room temperature. Water was added and the mixture was extracted with dichloromethane. After drying over anhydrous sodium sulfate, the solution was filtered through a short column of hydrous sodium magnesium silicate and further eluted with several volumes of dichloromethane. The combined organic phase was concentrated on a steam bath with the gradual addition of hexane until crystallization occurred. After cooling, the crystals were collected by filtration to yield the title compound (2.91 g), m.p. 107-108° C.

Aufarbeitung

  1. customthe volatiles removed at room temperature
  2. additionWater was added
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. filtrationthe solution was filtered through a short column of hydrous sodium magnesium silicate
  6. washfurther eluted with several volumes of dichloromethane
  7. concentrationThe combined organic phase was concentrated on a steam bath with the gradual addition of hexane until crystallization
  8. temperatureAfter cooling
  9. filtrationthe crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-f6371761bdcb4afd94be1f844baf2036
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06511974B1

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