Sodium Cyanide → 1-Cyanomethyl-3-methyl-4-phenylthiobenzene

HRID 37152Notes

Reaction equation

HRID 37152 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:5]([CH3:16])[CH:4]=1.[C-:17]#[N:18].[Na+]>CN(C)C=O.[Cl-].[Na+].O>[C:17]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:5]([CH3:16])[CH:4]=1)#[N:18]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 199346681-Chloromethyl-3-methyl-4-phenylthiobenzene

Product 1

HCID 199346671-Cyanomethyl-3-methyl-4-phenylthiobenzene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Thus obtained 1-chloromethyl-3-methyl-4-phenylthiobenzene was dissolved in 56 ml of N,N-dimethylformamide, and 18.16 g of finely ground sodium cyanide was added, and the mixture was stirred overnight at room temperature. After adding 300 ml of saturated brine and 300 ml of ice water to the reaction mixture, it was extracted with ethyl acetate (300 ml×3). The extract was washed with saturated brine (200 ml×3), and dried with anhydrous sodium sulfate, concentrated in vacuo, and 1-cyanomethyl-3-methyl-4-phenylthiobenzene was obtained (45.95 g).

Workup

  1. extractionwas extracted with ethyl acetate (300 ml×3)
  2. washThe extract was washed with saturated brine (200 ml×3)
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8921fb5be03740e0b38ffc31f96ed2a5
Source dataset
uspto-grants-1995_05
Patent number
US05420128

Reaction notes

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