P-Anisidine → N-[4-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridyl)benzoyl]-4-methoxy-aniline

HRID 1245210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1245210
[CH3:1][O:2][C:3]1[C:4](=[O:29])[C:5]([CH3:28])=[C:6]([CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[C:15]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH:14]=2)[C:7](=[O:11])[C:8]=1[O:9][CH3:10].[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=1.C(N(CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C>C(Cl)Cl.O>[CH3:1][O:2][C:3]1[C:4](=[O:29])[C:5]([CH3:28])=[C:6]([CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH:38][C:35]3[CH:36]=[CH:37][C:32]([O:31][CH3:30])=[CH:33][CH:34]=3)=[O:18])=[C:15]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH:14]=2)[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Komponenten

7

Edukt 4

HCID 7732P-AnisidineHCID 8471TriethylamineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 219191784-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridyl)benzoic Acid

Produkt 1

HCID 21919147N-[4-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridyl)benzoyl]-4-methoxy-anilineAusbeute 59,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridyl)benzoic acid (44 mg, 0.1119 mmol) was dissolved in methylene chloride (10 ml), then p-anisidine (28 mg, 0.2276 mmol), triethylamine (23 mg, 0.2277 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (38 mg, 0.1982 mmol) were added thereto at room temperature and the mixture was stirred for 16 hours. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water and dried and the solvent was evaporated therefrom. The residue was purified by preparative thin layer chromatography (methylene chloride:methanol=95:5) to give the title compound (33 mg, 0.0662 mmol, 59%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was evaporated
  5. customThe residue was purified by preparative thin layer chromatography (methylene chloride:methanol=95:5)

Quellen und Nachweise

ORD-Eintrag
ord-b8a56825ed4f4207a8f7ba0aaaeeb327
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07122543B2

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