N,N,N',N'-Tetramethylmethanediamine → HCID 20148900, Verbindung

Reaktionsgleichung

[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][Cl:14])[CH:5]=[CH:4][C:3]=1[O:16][CH3:17].[CH3:18][N:19]([CH2:21]N(C)C)[CH3:20].C(OC(=O)C)(=O)C.[OH-].[Na+]>>[CH3:18][N:19]([CH2:21][CH:10]([CH2:11][CH2:12][CH2:13][Cl:14])[C:9]([C:6]1[CH:5]=[CH:4][C:3]([O:16][CH3:17])=[C:2]([Cl:1])[C:7]=1[Cl:8])=[O:15])[CH3:20]

Komponenten

Edukt 4

HCID 5829N,N,N',N'-Tetramethylmethanediamine

HCID 7918Acetic Anhydride

HCID 14798Sodium Hydroxide

HCID 20148901HCID 20148901, Verbindung

Produkt 1

HCID 20148900HCID 20148900, Verbindung

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

2,3-Dichloro-4-(5-chloropentanoyl)anisole (29.5 g, 0.1 mole) and N,N,N',N'-tetramethyldiaminomethane (25.5 g, 0.249 mole) were stirred and heated at 50° C. and then acetic anhydride (36.8 g, 0.36 mole) was added dropwise with stirring at such a rate that the temperature rose to 100° C. After heating at 95° C. for an additional 2 hours, the mixture was kept at ambient temperature for 15 hours, poured into crushed ice (400 g), strongly basified with 10 normal sodium hydroxide and extracted with ether. The ether extract was dried over Na2SO4 and the solvent removed in vacuo to give 2-(dimethylaminomethyl)-5-chloro-1-(2,3-dichloro-4-methoxyphenyl)-1-pentanone as a viscous oil.