Methyl iodide → HCID 54136909, Verbindung

HRID 330192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 330192
[CH2:1]([NH:5][C:6](=[O:17])[CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2)[CH2:2][CH2:3][CH3:4].[H-].[Na+].I[CH3:21]>CN(C)C=O>[CH2:1]([NH:5][C:6](=[O:17])[CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:21])[CH:12]=[CH:11]2)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53914725HCID 53914725, Verbindung

Produkt 1

HCID 54136909HCID 54136909, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of N-butylindole-5-acetamide (1.0 g) in dimethylformamide (15 ml) was added to a slurry of sodium hydride (0.11 g) in dimethylformamide (7 ml) at 0° under a nitrogen atmosphere, stirred for 1 hr at 0° and treated with iodomethane (0.3 ml). The reaction was quenched with saturated ammonium chloride solution and diluted with water. The precipitate that formed was collected by filtration, washed with water, and dried under vaccum to give N-butyl-1-methyl-indole-5-acetamide (0.46 g, 43%) as a pale yellow powder: NMR (250 MHz, CDCl3): 0.84(t, 3H, N(CH2)3CH3), 1.38-1.17(m, 4H, NCH2 (CH2)2), 3.16(q, 2H, NCH2), 3.67(s, 2H, ArCH2), 3.80(s, 3H, NCH3), 5.43(br, 1H, NH), 6.45(d, 1H, H2 -indole).

Aufarbeitung

  1. customThe reaction was quenched with saturated ammonium chloride solution
  2. additiondiluted with water
  3. customThe precipitate that formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried under vaccum

Quellen und Nachweise

ORD-Eintrag
ord-3bed9257a9574a7eaf0444791fd23cbd
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04894386

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