Pyridine → N-(2,6-diisopropylphenyl)-N'-(4-tert-butylcyclohexyl)urea

HRID 37291

Reaktionsgleichung

Reaktionsgleichung von HRID 37291
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([NH2:11])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:23])[CH3:22])[C:16]=1[N:24]=[C:25]=[O:26])([CH3:14])[CH3:13].N1C=CC=CC=1>ClCCl>[CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:22])[CH3:23])[C:16]=1[NH:24][C:25]([NH:11][CH:8]1[CH2:7][CH2:6][CH:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:10][CH2:9]1)=[O:26])([CH3:13])[CH3:14]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 793964-tert-ButylcyclohexylamineHCID 922592,6-Diisopropylphenyl isocyanate

Produkt 1

HCID 19935041N-(2,6-diisopropylphenyl)-N'-(4-tert-butylcyclohexyl)ureaAusbeute 59,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1.6 g of 4-tert-butylcyclohexylamine in 15 ml of dichloromethane was added a solution of 2.2 g of 2,6-diisopropylphenylisocyanate in dichloromethane dropwise in the presence of pyridine at 0° C. Thereafter the mixture was stirred for 1.5 hours at room temperature and concentrated. The residue was partitioned between isopropyl ether and water, and the organic layer was successively washed with 0.5N hydrochloric acid, water and sodium sulfate solution. The organic layer was dried over magnesium sulfate and then distilled away. The resulting residue was crystallized from ethyl acetate to give 2.2 g of N-(2,6-diisopropylphenyl)-N'-(4-tert-butylcyclohexyl)urea, melting at 270° C.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue was partitioned between isopropyl ether and water
  3. washthe organic layer was successively washed with 0.5N hydrochloric acid, water and sodium sulfate solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. distillationdistilled away
  6. customThe resulting residue was crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-6a6b231c3e824992b74412a4122da314
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420164

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