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

HRID 53849

反応式

HRID 53849 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5c141c9bdd984689b832fcc33d073f7a
出典データセット
uspto-grants-1997_04
特許番号
US05621010

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