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

HRID 53849

Reaction equation

HRID 53849 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

HCID 19960591N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-hexyloxyphenyl)ureaYield 71.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5c141c9bdd984689b832fcc33d073f7a
Source dataset
uspto-grants-1997_04
Patent number
US05621010

Linked notes

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