Sodium hydride → 2-[2-(N-benzyl-N-methylamino)ethoxy]-5-methoxybenzaldehyde

HRID 1598318Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1598318
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].[CH2:14]([N:21]([CH2:23][CH2:24]Cl)[CH3:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C.C1(C)C=CC=CC=1>[CH2:14]([N:21]([CH2:23][CH2:24][O:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5])[CH3:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 31968N-benzyl-2-chloro-N-methylethanamineHCID 956952-Hydroxy-5-methoxybenzaldehyde

Produkt 1

HCID 189336082-[2-(N-benzyl-N-methylamino)ethoxy]-5-methoxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

In a similar manner to the previous example, a solution of 2-hydroxy-5-methoxybenzal dehyde (25.0 g) in DMF (50 ml) was added to a stirred suspension of sodium hydride (6.84 g of a 60% dispersion in mineral oil) in dry DMF (125 ml) at ambient temperature under nitrogen with stirring. The mixture was heated at 70° C. for 2 hours and then cooled to ambient temperature and a solution of N-benzyl-2-chloro-N-methylethylamine in toluene (75 ml) was added [prepared from 48.5 g of the hydrochloride salt]. The oil obtained after work up was distilled under vacuum to give 2-[2-(N-benzyl-N-methylamino)ethoxy]-5-methoxybenzaldehyde as an oil. A sample of this oil which boiled at 202°-206° C. at 0.65 mbar was dissolved in ether and acidified with ethereal hydrogen chloride. The precipitate was collected by filtration, washed with ether to give 2-[2-(N-benzyl-N-methylamino)ethoxy]-5-methoxybenzaldehyde hydrochloride, m.p. 167°-169° C.

Aufarbeitung

  1. customat ambient temperature
  2. temperaturecooled to ambient temperature
  3. customThe oil obtained after work
  4. distillationup was distilled under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6eb13bfabe3a4c0985e7cf87f04a35a2
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05736568

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