Water → HCID 20315352, compound

HRID 2419334Notes

Reaction equation

HRID 2419334 reaction equation
[C-]#[N:2].[Na+].[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[CH:12]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][CH2:14]S([O-])(=O)=O.O>CN(C)C=O>[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[CH:12]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][C:14]#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 86735889HCID 86735889, compound

Product 1

HCID 20315352HCID 20315352, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 11.3 g (0.23 mole) of sodium cyanide in 100 ml of dry dimethyl formamide (DMF) is added dropwise a solution of 50 g (0.154 mole) of 2-(2,4-dichlorophenyl)-hexylmethane sulfonate in 50 ml of DMF. The reaction mixture is stirred at 70° overnight. It is then poured into 500 ml of water and extracted with ether. The combined ether extracts are washed with water, then saturated saline solution and finally dried over magnesium sulfate. Solvent is evaporated under reduced pressure to give 37 g of crude product which is further purified by vacuum distillation (107.5°-110°/0.05 mm) to give 33.9 g (86%) of expected product.

Workup

  1. extractionextracted with ether
  2. washThe combined ether extracts are washed with water
  3. dry with materialsaturated saline solution and finally dried over magnesium sulfate
  4. customSolvent is evaporated under reduced pressure
  5. customto give 37 g of crude product which
  6. distillationis further purified by vacuum distillation (107.5°-110°/0.05 mm)

Sources & evidence

ORD record
ord-8bc45d25b2074ffdb227a9f78a48f6f8
Source dataset
uspto-grants-1978_08
Patent number
US04105762

Reaction notes

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