Sodium Cyanide → HCID 23457241, compound

HRID 1680151Notes

Reaction equation

HRID 1680151 reaction equation
Cl[CH2:2][C:3]1[C:7]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=2[Cl:16])=[CH:6][S:5][CH:4]=1.[C-:17]#[N:18].[Na+]>CS(C)=O>[Cl:16][C:10]1[C:11]([CH3:15])=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][C:7]1[C:3]([CH2:2][C:17]#[N:18])=[CH:4][S:5][CH:6]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 23457220HCID 23457220, compound

Product 1

HCID 23457241HCID 23457241, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

2.72 g (10 mmoles) of 3-chloromethyl-4-(2-chloro-3-methylanilino)thiophen in 15 ml of dimethylsulfoxide are added dropwise to a solution of 650 mg of sodium cyanide in 15 ml of dimethylsulfoxide at 40°. The mixture is stirred for a further three hours, poured onto water and extracted three times with ethyl acetate. The combined extracts are washed with 50 ml each of 6 N hydrochloric acid and water, dried and concentrated. Crude 4-(2-chloro-3-methylanilino)-3-thiophenacetonitrile is obtained as an oil.

Workup

  1. additionpoured onto water
  2. extractionextracted three times with ethyl acetate
  3. washThe combined extracts are washed with 50 ml each of 6 N hydrochloric acid and water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3342c590a7ab453898aaf2772b2e4526
Source dataset
uspto-grants-1981_06
Patent number
US04272507

Reaction notes

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