Sodium Cyanide → 4-(Methylsulfanyl)-2-(trifluoromethyl)aniline

HRID 1759597Notes

Reaction equation

HRID 1759597 reaction equation
[S:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1)[C:2]#N.[C-]#N.[Na+]>CO>[CH3:2][S:1][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11]([F:12])([F:13])[F:14])[CH:5]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 13070054HCID 13070054, compound

Product 1

HCID 130700554-(Methylsulfanyl)-2-(trifluoromethyl)anilineYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-thiocyano-2-trifluoromethylaniline (1.09 g., 0.005 mole) and sodium cyanide (0.125 g., 0.0025 mole) in methanol (50 ml) is refluxed for about 16 hours. Methanol is removed from the cool reaction mixture by evaporation under reduced pressure, the residue is taken up in methylene chloride, washed with water and dried. Removal of the drying agent and solvent gives the product as a yellow oil (1 g., 91 percent yield).

Workup

  1. customMethanol is removed from the cool reaction mixture by evaporation under reduced pressure
  2. washwashed with water
  3. customdried
  4. customRemoval of the drying agent and solvent

Sources & evidence

ORD record
ord-01217933859947ff99c6e3752d58ddf9
Source dataset
uspto-grants-1982_07
Patent number
US04341901

Reaction notes

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