Sulfuric Acid → N-(2,6-diisopropylphenyl)-N'-(2-hydroxy-3-(adamant-1-yl)-5-methylphenyl)-oxalamide

HRID 11736

Reaktionsgleichung

Reaktionsgleichung von HRID 11736
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:26])[C:15]([NH:17][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=1[OH:25])=[O:16])([CH3:3])[CH3:2].[CH2:27]1[CH:32]2[CH2:33][C:34]3(O)[CH2:36][CH:30]([CH2:31]2)[CH2:29][CH:28]1[CH2:35]3.OS(O)(=O)=O.C(OCC)(=O)C>C(Cl)Cl>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:26])[C:15]([NH:17][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([C:28]23[CH2:29][CH:30]4[CH2:36][CH:34]([CH2:33][CH:32]([CH2:31]4)[CH2:27]2)[CH2:35]3)[C:19]=1[OH:25])=[O:16])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 641521-AdamantanolHCID 21976138N-(2,6-diisopropylphenyl)-N'-(2-hydroxy-5-methylphenyl)-oxalamide

Produkt 1

HCID 21976140N-(2,6-diisopropylphenyl)-N'-(2-hydroxy-3-(adamant-1-yl)-5-methylphenyl)-oxalamideAusbeute 48,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-(2,6-Diisopropylphenyl)-N′-(2-hydroxy-5-methylphenyl)-oxalamide (5.59 g, 15.5 mmol, 1.0 eq), prepared according to the synthesis method described in Example 8, and 1-adamantol (2.83 g, 18.6 mmol, 1.2 eq) were dissolved in CH2Cl2 (150 ml), forming a suspension. To this suspension was then added concentrated H2SO4 (1 ml). After addition of the acid, the solids eventually went into solution. After stirring at room temperature for 24 hours, the TLC (9:1 hexanes:ethyl acetate, visualized by UV) showed that most of the starting material had gone to product. At this point, the solvent was removed under reduced pressure, and the resulting solids were redissolved in ethyl acetate (100 ml). The resulting solution was then washed with saturated NaHCO3 (3×50 ml, gas is evolved), and brine, then dried over MgSO4. The solvent was removed under reduced pressure, and the resulting solid was purified via column chromatography to give a product, light yellow solid (3.68 g, 7.5 mmol, 48%). 1H NMR (300 MHz, CDCl3) δ 9.51 (s, 1H), 8.77 (s, 1H), 7.84 (s, 1H), 7.37 (t, J=7.2 Hz 1H), 7.23 (d, J=7.5 Hz, 2H), 7.00 (d, J=2.1 Hz, 1H), 6.94 (d, J=1.8 Hz, 1H), 3.01 (septet, J=6.9, 2H), 2.29 (s, 3H), 2.18 (bs, 6H), 2.10 (bs, 3H), 1.80 (bs, 6H), 1.22 (d, J=6.9, 12H); 13C NMR (75 MHz, CDCl3) δ 158.3, 158.2, 146.2, 145.8, 140.6, 129.9, 129.2, 129.2, 126.8, 124.7, 123.8, 120.9, 40.7, 37.3, 37.1, 29.1, 29.0, 23.6, 20.8. Anal. Calcd for C31H40N2O3: C, 76.19; H, 8.25; N, 5.73. Found: C, 75.89; H, 8.42; N, 5.37.

Aufarbeitung

  1. customaccording to the synthesis method
  2. customforming a suspension
  3. additionAfter addition of the acid
  4. customAt this point, the solvent was removed under reduced pressure
  5. dissolutionthe resulting solids were redissolved in ethyl acetate (100 ml)
  6. washThe resulting solution was then washed with saturated NaHCO3 (3×50 ml, gas is evolved), and brine
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed under reduced pressure
  9. customthe resulting solid was purified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-12a00ad62efd4cb7a54190de30c181ed
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098278B2

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