Benzoyl chloride → N'-t-butyl-N-cyclohexenylcarbonyl-N'-benzoylhydrazine

HRID 21635

Reaktionsgleichung

Reaktionsgleichung von HRID 21635
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+].[C:10]1([C:16](Cl)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C=CC=CC=1.CCCCCC>[C:2]([N:6]([C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:7][C:16]([C:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=1)=[O:17])([CH3:5])([CH3:4])[CH3:3]

Komponenten

7

Edukt 4

HCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide3×HCID 81889tert-Butylhydrazine monohydrochlorideHCID 1420661-Cyclohexenecarbonyl chloride

Produkt 1

HCID 15451994N'-t-butyl-N-cyclohexenylcarbonyl-N'-benzoylhydrazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 8058HexaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a stirred suspension of t-butylhydrazine hydrochloride (0.86 g, 0.007M) in toluene (30 ml) was added 50% sodium hydroxide (0.55 g, 0.007M). After 15 minutes, the mixture was cooled to 5° C. and cyclohexenylcarbonyl chloride (1.0 g, 0.007M) and 50% sodium hydroxide (0.55 g, 0.007M) were added separately and simultaneously so as to maintain the reaction temperature below 10° C. After the addition, the reaction mixture was allowed to warm to room temperature and stirred for 1 hour. The mixture was diluted with hexane and the solid product isolated by filtration. This product (1.2 g, 0.006M) was dissolved in toluene (30 ml) and cooled on ice while stirring. To this mixture was added benzoylchloride (1.0 g, 0.007M) and 50% sodium hydroxide (1.3 g, 0.007M) simultaneously. After addition, the mixture was stirred for 1/2 hour, diluted with hexane and the solid product, N'-t-butyl-N-cyclohexenylcarbonyl-N'-benzoylhydrazine, was isolated by filtration.

Aufarbeitung

  1. temperaturesimultaneously so as to maintain the reaction temperature below 10° C
  2. additionAfter the addition
  3. temperatureto warm to room temperature
  4. customthe solid product isolated by filtration
  5. temperaturecooled on ice
  6. stirringwhile stirring
  7. additionAfter addition
  8. stirringthe mixture was stirred for 1/2 hour

Quellen und Nachweise

ORD-Eintrag
ord-afd9ef446bce4af0b9c4f598804702b2
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424333

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