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

HRID 849760

Reaktionsgleichung

Reaktionsgleichung von HRID 849760
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+].[CH:10]1([C:16](Cl)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]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]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:17])([CH3:5])([CH3:4])[CH3:3]

Komponenten

7

Edukt 4

HCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide3×HCID 75938Cyclohexanecarbonyl chlorideHCID 81889tert-Butylhydrazine monohydrochloride

Produkt 1

HCID 15294612N'-t-butyl-N-cyclohexylcarbonyl-N'-benzoylhydrazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 8058HexaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a stirred suspension of t-butylhydrazine hydrochloride (2.0 g, 0.016M) in toluene (30 ml) was added 50% sodium hydroxide (1.3 g, 0.016M). After 15 minutes, the mixture was cooled to 5° C. and cyclohexanecarbonylchloride (2.4 g, 0.016 M) and 50% sodium hydroxide (1.3 g, 0.016M) 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 hr. The mixture was diluted with hexane and the solid product isolated by filtration. This product (1.5 g, 0.008M) was dissolved in a stirred mixture of toluene (30 ml) and cooled on ice. To this mixture was added benzoylchloride (1.1 g, 0.008 M) and 50% sodium hydroxide (0.6 g, 0.008M) simultaneously. After addition, the mixture was stirred for 1/2 hr., diluted with hexane and the solid product, N'-t-butyl-N-cyclohexylcarbonyl-N'-benzoylhydrazine, 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. additionAfter addition
  7. stirringthe mixture was stirred for 1/2 hr

Quellen und Nachweise

ORD-Eintrag
ord-907ad241e45742ceb11fb3a60dda9d88
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06013836

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