Sodium Cyanide → 2-Thiophenepropanenitrile

HRID 1614584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1614584
C1(C)C=CC(S(O[CH2:11][CH2:12][C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)(=O)=O)=CC=1.[C-:19]#[N:20].[Na+]>CS(C)=O>[S:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[CH2:12][CH2:11][C:19]#[N:20]

Komponenten

4

Edukt 2

HCID 8929Sodium CyanideHCID 36820342-Thiopheneethanol tosylate

Produkt 1

HCID 5664252-Thiophenepropanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture was prepared from 20.8 g of 2-[2-(4-toluenesulfonyloxy)ethyl]thiophene, 5.4 g of sodium cyanide and 175 ml of dimethylsulfoxide and this mixture was heated to 90° C. The mixture was quenched by pouring it into saturated aqueous ammonium chloride solution and the resulting solution was extracted into ethyl acetate. The ethyl acetate solution was dried over sodium sulfate and the solvent was evaporated under reduced pressure to give crude 2-thiophenepropionitrile. This product was mixed with 175 ml of 1M diborane in tetrahydrofuran and allowed to stir at room temperature. The reaction was quenched in ethanol and methanolic hydrogen chloride was added. The white solid which formed was separated by filtration, washed with ether and dried in a vacuum oven to give 3-(2-thienyl)propylamine hydrochloride melting at about 197-°198° C.

Aufarbeitung

  1. customThe mixture was quenched
  2. additionby pouring it into saturated aqueous ammonium chloride solution
  3. extractionthe resulting solution was extracted into ethyl acetate
  4. dry with materialThe ethyl acetate solution was dried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-eab2906058904eaa8415815ff9b4ca49
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05198457

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