Sodium Chloride → HCID 53988712, compound

HRID 621644Notes

Reaction equation

HRID 621644 reaction equation
Cl[CH2:2][C:3]1[C:4]([F:12])=[CH:5][C:6]([S:10][CH3:11])=[C:7]([CH3:9])[CH:8]=1.[C-:13]#[N:14].[Na+].[Cl-].[Na+]>>[C:13]([CH2:2][C:3]1[C:4]([F:12])=[CH:5][C:6]([S:10][CH3:11])=[C:7]([CH3:9])[CH:8]=1)#[N:14]

Participants

4

Reactant 3

HCID 5234Sodium ChlorideHCID 8929Sodium CyanideHCID 21242813HCID 21242813, compound

Product 1

HCID 53988712HCID 53988712, compound

Procedure

5-Chloromethyl-4-fluoro-2-methylthiotoluene (21 g) is dissolved in N,N-dimemthylformamide (90 ml), and thereto is added finely divided sodium cyanide (6.03 g), and the mixture is stirred at room temperature for 18 hours. 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 5-cyanomethyl-4-fluoro-2-methylthiotoluene.

Workup

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

Sources & evidence

ORD record
ord-19d01bc83f27496bbda0ac76219e02ef
Source dataset
uspto-grants-1989_04
Patent number
US04824834

Reaction notes

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