2-Chlorobenzoxazole → N-(Benzoxazol-2-yl)-N-3-(4-methoxyphenoxy)propyl-3-tert-butyldimethylsilyloxybenzylamine

HRID 2215186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215186
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([O:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:14]=2)=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.Cl[C:39]1[O:40][C:41]2[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=2[N:43]=1>CN(C)C=O>[O:40]1[C:41]2[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=2[N:43]=[C:39]1[N:11]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][Si:20]([C:23]([CH3:24])([CH3:25])[CH3:26])([CH3:21])[CH3:22])[CH:14]=1)[CH2:10][CH2:9][CH2:8][O:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:28][CH:27]=1

Komponenten

5

Edukt 3

HCID 119862-ChlorobenzoxazoleHCID 81531DiisopropylethylamineHCID 21949684n-3-(4-Methoxyphenoxy)propyl-3-tert-butyldimethylsilyloxybenzylamine

Produkt 1

HCID 21949679N-(Benzoxazol-2-yl)-N-3-(4-methoxyphenoxy)propyl-3-tert-butyldimethylsilyloxybenzylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N-3-(4-methoxyphenoxy)propyl-3-tert-butyldimethylsilyloxybenzylamine (1.9 g, 5.0 mmol) was dissolved in N,N-dimethylformamide (3.0 mL). Subsequently, N,N-diisopropylethylamine (768 mg, 5.9 mmol) was added dropwise thereto. To the solution, 2-chlorobenzoxazole (912 mg, 5.94 mmol) was added. The mixture was stirred for 15 minutes at room temperature, and then stirred overnight at 70° C. The resultant mixture was extracted with ethyl acetate, followed by washing the organic layer with brine, drying over anhydrous sodium sulfate, and concentration under reduced pressure. The resultant mixture was subjected to purification by silica gel column chromatography (n-hexane/ethyl acetate=10/1), whereby the target compound was obtained (1.9 g, 73%).

Aufarbeitung

  1. stirringstirred overnight at 70° C
  2. extractionThe resultant mixture was extracted with ethyl acetate
  3. washby washing the organic layer with brine
  4. dry with materialdrying over anhydrous sodium sulfate, and concentration under reduced pressure
  5. customThe resultant mixture was subjected to purification by silica gel column chromatography (n-hexane/ethyl acetate=10/1), whereby the target compound
  6. customwas obtained (1.9 g, 73%)

Quellen und Nachweise

ORD-Eintrag
ord-0925f329851543c29b0a66809d97d3d7
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109226B2

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