Sodium Cyanide → HCID 20343961, compound

HRID 2049686Notes

Reaction equation

HRID 2049686 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[CH2:11]Cl)=[CH:4][CH:3]=1.[C-:17]#[N:18].[Na+]>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[CH2:11][C:17]#[N:18])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 20343965HCID 20343965, compound

Product 1

HCID 20343961HCID 20343961, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

12.0 g of 2-(4-fluorophenylthio)benzyl chloride are added portionwise over a 30 minute span to a mixture of 2.9 g of sodium cyanide in 120 ml of dimethylsulfoxide. After total addition, the reaction mixture is stirred for 26 hours before being poured onto 150-200 ml of crushed ice. The mixture is extracted four times with 70 ml portions of ether and the combined ether extracts are successively washed four times with 50 ml portions of water, washed once with 25 ml of a saturated sodium chloride solution and dried, providing 2-(4-fluorophenylthio)benzyl cyanide.

Workup

  1. additionAfter total addition
  2. extractionThe mixture is extracted four times with 70 ml portions of ether
  3. washthe combined ether extracts are successively washed four times with 50 ml portions of water
  4. washwashed once with 25 ml of a saturated sodium chloride solution
  5. customdried

Sources & evidence

ORD record
ord-f425eeb89def4edc87b2988aec7ecbd0
Source dataset
uspto-grants-1980_04
Patent number
US04198420

Reaction notes

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