alpha-(5-Iodopentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrile → alpha-(3,4-Dimethoxypheny)1,3-dihydro-alpha-[(4-methylphenyl)thio]-1,3-dioxo-2H-isoindole-2-heptanenitrile

HRID 1078747Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1078747
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([S:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)[C:8]#[N:9].[C:28]1(=[O:38])[NH:32][C:31](=[O:33])[C:30]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:29]12.[K]>CN(C)C=O>[CH3:19][O:18][C:12]1[CH:11]=[C:10]([C:7]([S:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:32]2[C:28](=[O:38])[C:29]3[C:30](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:31]2=[O:33])[C:8]#[N:9])[CH:15]=[CH:14][C:13]=1[O:16][CH3:17]

Komponenten

4

Edukt 2

HCID 19042083alpha-(5-Iodopentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrileHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 10673372alpha-(3,4-Dimethoxypheny)1,3-dihydro-alpha-[(4-methylphenyl)thio]-1,3-dioxo-2H-isoindole-2-heptanenitrileAusbeute 77,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 6.12 g of α-(5-iodopentyl)-3,4-dimethoxy-α-[(4-methylphenyl)thio]benzeneacetonitrile and 2.22 g of potassium phthalimide and 50 mL of N,N-dimethylformamide is heated on a steam bath for 2 hours. The reaction solution is concentrated in vacuo and the residue is distributed between diethyl ether-water, with agitation. The organic layer is washed with 1N sodium hydroxide, followed by aqueous potassium bicarbonate. The solution is dried (sodium sulfate), and the volatiles removed in vacuo. Chromatography on silica gel, with gradient elution progressing from hexane to chloroform to methyl alcohol, affords 4.77 g of the desired product as a fluorescent oil.

Aufarbeitung

  1. temperatureis heated on a steam bath for 2 hours
  2. concentrationThe reaction solution is concentrated in vacuo
  3. washThe organic layer is washed with 1N sodium hydroxide
  4. dry with materialThe solution is dried (sodium sulfate)
  5. customthe volatiles removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b8e13044b81e4f99a9b978e0a9f876f6
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05550149

Notizen zur Reaktion

Wird geladen…