Benzyl Chloride → HCID 10454683, Verbindung

HRID 2370423

Reaktionsgleichung

Reaktionsgleichung von HRID 2370423
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13].[H-].[Na+].[H][H].[CH2:21](Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH2:21]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([I:1])=[CH:10][CH:9]=2)[C:5]([CH2:11][C:12]([N:14]([CH3:15])[CH3:16])=[O:13])=[CH:6]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

6

Edukt 4

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 102459112-(5-iodo-1H-indol-3-yl)-N,N-dimethyl-acetamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 10454683HCID 10454683, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(5-Iodo-1H-indol-3-yl)-N,N-dimethyl-acetamide (24.7 g, 75.4 mmol) in DMF (90 mL), under an inert atmosphere sodium hydride (1.91 g 95%, 75.4 mmol) is added which leads to the formation of a pale yellow solution. When the evolution of hydrogen has ceased, benzyl chloride (9.54 g, 75.4 mmol) is added in three portions over a period of 10 minutes. The mixture warms to 60° C., and after stirring for one hour a suspension forms. On the rotavapor, a part of the DMF (about 80 mL) is removed, which leads to crystallization of the product. Water (300 mL) is added, and the crystallized product is triturated at 80° C. for one hour on the rotavapor. The product is filtered off, washed twice with water (200 mL each washing), and dried to give 26.8 g (85%) of the title compound as pale yellow crystals, mp=167-168° C. From the mother liquor, another crop (2.6 g, 8%) is obtained which is also pure. 1H-NMR (DMSO-D6, 300 MHz) δ 3.33, 3.72 (2 s, 3H each, N(CH3)2); 3.72 (s, 2H, CH2CO); 5.34 (CH2Ph); 7.08-7.15, 7.15-7.30 (2 m, 5H, Ph); 7.24 (d, 3J=8.7 Hz, H-7); 7.26 (s, 1H, H-2); 7.32 (dd, 4J=1.3 Hz, H-6); 7.94 (d, 1H, H-4). 13C-NMR (DMSO-D6, 75 MHz) δ 30.90 (CH2CO); 35.72, 37.89 (N(CH3)2); 49.70 (CH2Ph); 83.31 (C-5); 108.61 (C-3); 113.26 (C-2); 127.65 (2 Ph-C); 128.06 (C-6 or Ph C-4); 128.53 (C-4); 129.19 (Ph C-4 or C-6); 129.22 (2 Ph-C); 129.83 (C-7); 131.38 (Ph ipso-C); 135.79 (C-9); 138.67 (C-8); 170.82 (CONMe2).

Aufarbeitung

  1. customwarms to 60° C.
  2. customOn the rotavapor, a part of the DMF (about 80 mL) is removed
  3. customwhich leads to crystallization of the product
  4. additionWater (300 mL) is added
  5. customthe crystallized product is triturated at 80° C. for one hour on the rotavapor
  6. filtrationThe product is filtered off
  7. washwashed twice with water (200 mL each washing)
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7a720cb3423b459b882767d5664d7c88
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710093B2

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