Triethylamine → N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-hexyloxyphenyl)urea

HRID 53849

Reaktionsgleichung

Reaktionsgleichung von HRID 53849
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[CH2:18]([O:24][C:25]1[CH:33]=[CH:32][C:28](C(O)=O)=[CH:27][CH:26]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C([N:36]([CH2:39]C)CC)C.[NH2:41][C:42]1[CH:64]=[CH:63][CH:62]=[CH:61][C:43]=1[CH2:44][CH2:45][C:46]1[CH:51]=[C:50]([C:52]([CH3:55])([CH3:54])[CH3:53])[C:49]([OH:56])=[C:48]([C:57]([CH3:60])([CH3:59])[CH3:58])[CH:47]=1>C1(C)C=CC=CC=1>[C:57]([C:48]1[CH:47]=[C:46]([CH:51]=[C:50]([C:52]([CH3:55])([CH3:53])[CH3:54])[C:49]=1[OH:56])[CH2:45][CH2:44][C:43]1[CH:61]=[CH:62][CH:63]=[CH:64][C:42]=1[NH:41][C:39]([NH:36][C:28]1[CH:27]=[CH:26][C:25]([O:24][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:33][CH:32]=1)=[O:8])([CH3:58])([CH3:60])[CH3:59]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 708344-(Hexyloxy)benzoic acidHCID 199401P,P-Diphenylphosphinic azideHCID 199604694-(2-Aminophenethyl)-2,6-di-tert-butylphenol

Produkt 1

HCID 19960591N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-hexyloxyphenyl)ureaAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of diphenylphosphorylazide (0.93 g, 3.4 mmol), 4-hexyloxybenzoic acid (0.68 g, 3.1 mmol) and triethylamine (0.34 g, 3.4 mmol) in toluene (10 ml) was stirred at room temperature for 3.5 hrs and heated at about 90° C. for 2 hrs with stirring. After allowing the mixture to cool (under 0° C.), a solution of 4-(2-aminophenethyl)-2,6-di-tert-butylphenol (1.0 g, 3.1 mmol) in toluene (4 ml) was added dropwise. The solution was warmed up to room temperature and stirred overnight. After distilling off the solvent and purification of the residue by a silica gel column chromatography, recrystallization from ethyl acetate/hexane afforded N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-hexyloxyphenyl)urea (1.2 g, 71% yield). m.p. 174°-176° C.

Aufarbeitung

  1. temperatureto cool (under 0° C.)
  2. temperatureThe solution was warmed up to room temperature
  3. stirringstirred overnight
  4. distillationAfter distilling off
  5. customthe solvent and purification of the residue
  6. customby a silica gel column chromatography, recrystallization from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-5c141c9bdd984689b832fcc33d073f7a
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05621010

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