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

HRID 621641Notes

Reaction equation

HRID 621641 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+].[Cl-].[Na+]>>[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

4

Reactant 3

HCID 5234Sodium ChlorideHCID 8929Sodium CyanideHCID 199346681-Chloromethyl-3-methyl-4-phenylthiobenzene

Product 1

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

Procedure

The 1-chloromethyl-3-methyl-4-phenylthiobenzene obtained above is dissolved in N,N-dimemthylformamide (56 ml), and thereto is added finely divided sodium cyanide (18.16 g), and the mixture is stirred at room temperature overnight. To the reaction mixture are added saturated aqueous sodium chloride solution (300 ml) and ice water (300 ml), and the mixture is extracted with ethyl acetate (300 ml×3). The combined extracts are washed with saturated aqueous sodium chloride solution (200 ml×3), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 1-cyanomethyl-3-methyl-4phenylthiobenzene (45.95 g).

Workup

  1. dissolutionabove is dissolved in N,N-dimemthylformamide (56 ml)
  2. extractionthe mixture is extracted with ethyl acetate (300 ml×3)
  3. washThe combined extracts are washed with saturated aqueous sodium chloride solution (200 ml×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3d4f818ae6e04d67862bb1e5bb89dc12
Source dataset
uspto-grants-1989_04
Patent number
US04824834

Reaction notes

Loading…