2-Aminophenol → N-(2,6-diisopropylphenyl)-N'-(2-hydroxyphenyl)-oxalamide

HRID 1823185

반응식

HRID 1823185 반응식
C(O[C:4](=[O:26])[C:5]([N:7]([C:14]1[C:19]([CH:20]([CH3:22])[CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=1[CH:23]([CH3:25])[CH3:24])C1C=CC=CC=1)=[O:6])C.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[OH:34].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH:20]([C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:23]([CH3:24])[CH3:25])[C:14]=1[NH:7][C:5](=[O:6])[C:4]([NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[OH:34])=[O:26])([CH3:21])[CH3:22]

참가 물질

5

반응물 3

HCID 58012-AminophenolHCID 8471TriethylamineHCID 68533759N-(2,6-Diisopropylphenyl)-oxanilic acid ethyl ester

생성물 1

HCID 21976139N-(2,6-diisopropylphenyl)-N'-(2-hydroxyphenyl)-oxalamide수율 85%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

N-(2,6-Diisopropylphenyl)-oxanilic acid ethyl ester (2.78 g, 10 mmol, 1 eq) and 2-aminophenol (1.31 g, 12 mmol, 1.2 eq) were dissolved in toluene (50 ml), forming a suspension. To this suspension was added triethylamine (2.78 ml, 20 mmol, 2 eq). The suspension was then heated to reflux, causing the solids to dissolve. After heating at reflux overnight, the product precipitated. At this point, ethyl acetate was added until the precipitate redissolved. The solution was then washed with 2 M HCl solution (2×100 ml). The aqueous layer was then washed with ethyl acetate, and the combined organic layers were washed with brine (100 ml), and dried over MgSO4. The solvent was then removed under reduced pressure, leaving a yellowish solid. The yellowish solid was then recrystallized from toluene, producing a product, white crystalline solid (2.9 g, 8.5 mmol, 85% yield). 1H NMR (300 MHz, CDCl3) δ 9.67 (s, 1H), 8.84 (s, 1H), 8.12 (s, 1H), 7.50 (dd, J=8.25, 1.8 Hz 1H), 7.37 (t, J=7.2 Hz, 1H), 7.23 (d, J=7.5 Hz, 1H), 7.16 (dt, J=7.7, 1.5 Hz, 1H), 6.95 (comp m, 2H), 3.03 (septet, J=6.6 Hz, 2H), 1.22 (d, J=6.9, 12H); 13C NMR (75 MHz, CDCl3) δ 158.9, 158.2, 148.2, 146.1, 129.4, 127.9, 124.2, 124.0, 122.3, 121.2, 119.1, 29.2, 23.9. Anal. Calcd for C20H24N2O3: C, 70.56; H, 7.11; N, 8.23; O, 14.10. Found: C, 34.90; H, 4.64; N, 5.79.

후처리

  1. customforming a suspension
  2. temperatureThe suspension was then heated
  3. temperatureto reflux
  4. dissolutionto dissolve
  5. temperatureAfter heating
  6. temperatureat reflux overnight
  7. customthe product precipitated
  8. additionAt this point, ethyl acetate was added until the precipitate
  9. dissolutionredissolved
  10. washThe solution was then washed with 2 M HCl solution (2×100 ml)
  11. washThe aqueous layer was then washed with ethyl acetate
  12. washthe combined organic layers were washed with brine (100 ml)
  13. dry with materialdried over MgSO4
  14. customThe solvent was then removed under reduced pressure
  15. customleaving a yellowish solid
  16. customThe yellowish solid was then recrystallized from toluene

출처 및 근거

ORD 기록
ord-49989f465c5a455f804d9ab8de04b724
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07037987B2

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