Pyridine → N1-(4-methoxybenzoyl)-N2-(4-propylbenzoyl)-4-(tert-butyldimethylsilyloxy)-1,2-benzenediamine

HRID 395724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 395724
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([C:7]([NH:9][C:10]2[C:11]([NH2:24])=[CH:12][C:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[CH:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1.N1C=CC=CC=1.[CH2:33]([C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=1)[CH2:34][CH3:35]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:24][C:40](=[O:41])[C:39]3[CH:43]=[CH:44][C:36]([CH2:33][CH2:34][CH3:35])=[CH:37][CH:38]=3)=[CH:12][C:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:21])[CH3:22])([CH3:19])[CH3:18])=[CH:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 1042934-Propylbenzoyl chlorideHCID 54024338N1-(4-methoxybenzoyl)-4-(tert-butyldimethylsilyloxy)-1,2-benzenediamine

Produkt 1

HCID 54350608N1-(4-methoxybenzoyl)-N2-(4-propylbenzoyl)-4-(tert-butyldimethylsilyloxy)-1,2-benzenediamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of N1-(4-methoxybenzoyl)-4-(tert-butyldimethylsilyloxy)-1,2-benzenediamine (300 mg, 0.81 mmol) in methylene chloride (20 mL) was added pyridine (0.13 mL, 1.6 mmol) followed by 4-propylbenzoyl chloride (0.15 mL, 0.89 mmol). The reaction mixture was stirred for 4 h, diluted with methylene chloride, washed with saturated aqueous cupric sulfate solution, dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was chromatographed (silica gel, methylene chloride to 20% ethyl acetate/80% methylene chloride) to give 400 mg (95%) of the the title compound as a solid.

Aufarbeitung

  1. washwashed with saturated aqueous cupric sulfate solution
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed (silica gel, methylene chloride to 20% ethyl acetate/80% methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-da33919a10a548e380113f33dfea8aa2
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06605626B2

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