4-(4-Iodophenyl)benzonitrile → 4'-Mercaptobiphenyl-4-carbonitrile

HRID 6015

Reaktionsgleichung

Reaktionsgleichung von HRID 6015
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C[S-:17].[Na+]>CN(C)P(N(C)C)(N(C)C)=O>[SH:17][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 13930054-(4-Iodophenyl)benzonitrileHCID 4378561Sodium methanethiolate

Produkt 1

HCID 147953354'-Mercaptobiphenyl-4-carbonitrileAusbeute 106,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 12679HexamethylphosphoramideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

3.25 g (10.8.10-3 mol) of 4-(4-iodophenyl)benzonitrile are dissolved in 50 ml of hexamethylphosphoramide, and 3.05 g (43.4.10-3 mol) of sodium thiomethylate are then added to the solution. The reaction mixture is heated at 100° C. for 1.5 hours and then, after cooling, hydrolyzed in a 1 N hydrochloric acid/ice mixture. The expected product is extracted with ethyl acetate. The resulting organic phase is washed with water until the pH of the washings is neutral, dried over magnesium sulfate and then evaporated under reduced pressure to give 2.4 g (quantitative yield) of a pale yellow solid.

Aufarbeitung

  1. extractionThe expected product is extracted with ethyl acetate
  2. washThe resulting organic phase is washed with water until the pH of the washings
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b40073ab084446aca3ddff0719ca2133
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246961

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