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

HRID 11732

Reaction equation

HRID 11732 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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); 3C 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.

Workup

  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

Sources & evidence

ORD record
ord-df4772e58b434195849347b87ca8e552
Source dataset
uspto-grants-2006_08
Patent number
US07098278B2

Linked notes

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