2-amino-N-(4-isopropylphenyl)benzamide → HCID 46841009, Verbindung

HRID 1846308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846308
[NH2:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=1)=[O:5].[OH:20][CH2:21][CH2:22][O:23][C:24]1[C:31]([CH3:32])=[CH:30][C:27]([CH:28]=O)=[CH:26][C:25]=1[CH3:33]>C(O)C.[Cu](Cl)Cl>[OH:20][CH2:21][CH2:22][O:23][C:24]1[C:31]([CH3:32])=[CH:30][C:27]([C:28]2[N:6]([C:7]3[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=3)[C:4](=[O:5])[C:3]3[C:2](=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:1]=2)=[CH:26][C:25]=1[CH3:33]

Komponenten

5

Edukt 2

HCID 28065462-amino-N-(4-isopropylphenyl)benzamideHCID 289325784-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde

Produkt 1

HCID 46841009HCID 46841009, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24014Cupric ChlorideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-N-(4-isopropylphenyl)benzamide (0.400 g, 1.57 mmol) and 4-(2-hydroxyethoxy)-3,5-dimethylbenzaldehyde (0.30 g, 1.57 mmol) in anhydrous ethanol (20 mL) was added anhydrous copper (II) chloride (0.63 g, 4.71 mmol). The reaction mixture was stirred at reflux for 4 hours under nitrogen. The solvent was removed and the residue was diluted with dichloromethane (150 mL) and water (100 mL). The organic phase was separated and further washed with water (100 mL), brine (100 mL), and dried over sodium sulfate. The crude mixture was purified by column chromatography on silica gel (230-400 mesh) using hexane/ethyl acetate (1:1) as eluent to give the title compound as a white solid. Yield: 100 mg (15.6%). MP 160-162° C. 1H-NMR (400 Hz, CDCl3): δ 8.34 (d, J=7.6 Hz, 1H), 7.80 (m, 2H), 7.52 (m, 1H), 7.17 (d, J=8.4 Hz, 2H), 7.05 (d, J=8.4 Hz, 2H), 6.97 (s, 2H), 3.90 (m, 2H), 3.78 (t, J=4.8 Hz, 2H), 2.86 (m, 1H), 2.13 (s, 6H), 2.06 (t, J=6.4 Hz, 1H), 1.20 (d, J=7.2 Hz, 3H). MS (ES+) m/z: 429.52 (M+1).

Aufarbeitung

  1. temperatureat reflux for 4 hours under nitrogen
  2. customThe solvent was removed
  3. additionthe residue was diluted with dichloromethane (150 mL) and water (100 mL)
  4. customThe organic phase was separated
  5. washfurther washed with water (100 mL), brine (100 mL)
  6. dry with materialdried over sodium sulfate
  7. customThe crude mixture was purified by column chromatography on silica gel (230-400 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-5379a414644f4ef791f40c634ade8849
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952021B2

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