3-(4-Cyanophenyl)propyl methanesulfonate → 4-(3-Phthalimidopropyl)benzonitrile

HRID 485279Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 485279
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].S(O[CH2:18][CH2:19][CH2:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1)(C)(=O)=O>CN(C=O)C>[C:1]1(=[O:11])[N:5]([CH2:18][CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:25]#[N:26])=[CH:27][CH:28]=2)[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Komponenten

4

Edukt 2

HCID 219936463-(4-Cyanophenyl)propyl methanesulfonateHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 134213034-(3-Phthalimidopropyl)benzonitrileAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To 100 ml of DMF suspension of 21.1 g (0.114 mol) of potassium phthalimide was added 50 ml of DMF solution of 13.6 g (57 mmols) of crude 4-(3-mesyloxypropyl)benzonitrile. The reaction mixture was stirred at 90° C. for 3 hours, then cooled to room temperature and poured into 200 ml of ice-water, followed by extraction with ether-benzene (1:1). The organic layer was dried over Na2SO4 and concentrated, giving 14.0 g (yield 85%) of 4-(3-phthalimidopropyl)benzonitrile.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. extractionfollowed by extraction with ether-benzene (1:1)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-263442db364047469babe0d857cfd484
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04536391

Notizen zur Reaktion

Wird geladen…