4-tert-Butylcyclohexanone → tert-butyl N-[(4-tert-butylcyclohexylidene)amino]carbamate

HRID 2218967

Reaktionsgleichung

Reaktionsgleichung von HRID 2218967
[C:1]([CH:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[NH:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[NH2:13].[O-]S([O-])(=O)=O.[Mg+2].[O-]S([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl.CC#N>[C:17]([O:16][C:14]([NH:12][N:13]=[C:8]1[CH2:9][CH2:10][CH:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6][CH2:7]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Komponenten

6

Edukt 3

HCID 73924-tert-ButylcyclohexanoneHCID 70091tert-Butyl carbazateHCID 13828231HCID 13828231, Verbindung

Produkt 1

HCID 288080tert-butyl N-[(4-tert-butylcyclohexylidene)amino]carbamateAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-tert-butylcyclohexanone (3.95 g, 25.6 mmol) in CH2Cl2 (50 mL) was added tert-butyl hydrazinecarboxylate (3.83 g, 25.6 mmol). A 1:1 mixture of MgSO4/Na2SO4 was added to the reaction to make a slurry and the reaction was stirred vigorously. After 18 h, the reaction was diluted with CH3CN and filtered. The solvent was removed from the filtrate under reduced pressure to give 6.78 g of N′-(4-tert-butyl-cyclohexylidene)-hydrazinecarboxylic acid tert-butyl ester as a white foam. This material was used without further purification in the next step. 1H NMR (400 MHz, DMSO-d6) δ 9.51 (s, 1H), 2.93 (d, J=15 Hz, 1H), 2.30 (d, J=13 Hz, 1H), 2.08 (m, 1H), 1.89 (m, 2H), 1.66 (m, 1H), 1.43 (s, 9H), 1.25 (m, 1H), 1.13 (m, 1H), 1.03 (m, 1H), 0.85 (s, 9H).

Aufarbeitung

  1. additionwas added to the reaction
  2. filtrationfiltered
  3. customThe solvent was removed from the filtrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-567a1aff1b3b4d1c8fe24a80795ebd27
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07414040B2

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