Sodium Cyanide → 2-Thiophenepropanenitrile

HRID 345626Notes

Reaction equation

HRID 345626 reaction equation
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]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 36820342-Thiopheneethanol tosylate

Product 1

HCID 5664252-Thiophenepropanenitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-883d472a656e4287a3a7e4130a00e646
Source dataset
uspto-grants-1991_10
Patent number
US05057613

Reaction notes

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