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

HRID 53849

반응식

HRID 53849 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5c141c9bdd984689b832fcc33d073f7a
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05621010

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