Triethylamine → N-(2,6-diisopropylphenyl)-N'-(2-hydroxy-5-methylphenyl)-oxalamide

HRID 1823188ノート

反応式

HRID 1823188 の反応式
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][C:31](C)=[CH:30][C:29]=1[OH:35].[CH2:36](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]=[C:32]([CH3:36])[CH:31]=[CH:30][C:29]=1[OH:35])=[O:26])([CH3:21])[CH3:22]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 760822-Amino-5-methylphenolHCID 68533759N-(2,6-Diisopropylphenyl)-oxanilic acid ethyl ester

生成物 1

HCID 21976138N-(2,6-diisopropylphenyl)-N'-(2-hydroxy-5-methylphenyl)-oxalamide収率 90%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

N-(2,6-Diisopropylphenyl)-oxanilic acid ethyl ester (5.14 g, 18.5 mmol, 1.0 eq) and 2-amino-5-methylphenol (2.28 g, 18.5 mmol, 1 eq) were dissolved in toluene (50 ml), forming a suspension. To this suspension was then added triethylamine (2.6 ml, 18.5 mmol, 1 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 (5.90 g, 16.6 mmol, 90% yield). 1H NMR (300 MHz, CDCl3) δ 9.58 (s, 1H), 8.81 (s, 1H), 7.92 (s, 1H), 7.37 (t, J=7.8 Hz 1H), 7.27 (d, J=0.9 Hz, 1H), 7.23 (d, J=7.8 Hz, 2H), 6.97 (dd, J=8.1, 2.1 Hz, 1H), 6.90 (d, J=8.1 Hz, 1H), 3.02 (septet, J 6.6, 2H), 2.29 (s, 3H), 1.22 (d, J=7.2, 12H); 13C NMR (75 MHz, CDCl3) δ 158.8, 158.2, 146.0, 130.7, 129.4, 128.7, 124.0, 123.8, 122.6, 119.1, 29.2, 23.9, 20.7. Anal. Calcd for C21H26N2O3: C, 71.16; H, 7.39; N, 7.90. Found: C, 70.85; H, 7.68; N, 7.73.

後処理

  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

出典と根拠

ORDレコード
ord-fa03c7748fc14f5ba3c3e9708d91583d
出典データセット
uspto-grants-2006_05
特許番号
US07037987B2

反応ノート

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