Sodium Cyanide → HCID 86748800, compound

HRID 1647943Notes

Reaction equation

HRID 1647943 reaction equation
[C-:1]#[N:2].[Na+].[Cl:4][C:5]1[CH:6]=[C:7]([CH:22](Br)[CH3:23])[CH:8]=[CH:9][C:10]=1[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]21[O:21][CH2:20][CH2:19][O:18]2>O.CS(C)=O>[Cl:4][C:5]1[CH:6]=[C:7]([CH:22]([CH3:23])[C:1]#[N:2])[CH:8]=[CH:9][C:10]=1[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]21[O:21][CH2:20][CH2:19][O:18]2

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 86748799HCID 86748799, compound

Product 1

HCID 86748800HCID 86748800, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

7.35 g of sodium cyanide were dissolved in 10 ml of water under heat, incorporated with 60 ml of dimethylsulfoxide, cooled to room temperature and then incorporated with a solution of 51 g of 1-[3-chloro-4-(2,2-ethylenedioxycyclohexane-1-yl methyl)phenyl]ethyl bromide in 90 ml of dimethylsulfoxide. The reaction mixture obtained was agitated at 70° C. for one hour, thereafter incorporated with water and extracted with ethyl acetate. The extract was washed with water, dried and then freed of the solvent at a reduced pressure to obtain a residue. The thus obtained residue was adhered to a silica gel-packed column and then eluted with isopropyl ether hexane (2/1). The eluate obtained was freed of the solvent thereby to obtain 32.7 g of 2-[3-chloro-4-(2,2-ethylenedioxycyclohexane-1-yl methyl)phenyl]propionitrile.

Workup

  1. temperatureunder heat
  2. customThe reaction mixture obtained
  3. extractionincorporated with water and extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customto obtain a residue
  7. washeluted with isopropyl ether hexane (2/1)
  8. customThe eluate obtained

Sources & evidence

ORD record
ord-4087cd92d0ff4958bbc57a710cafdc45
Source dataset
uspto-grants-1995_07
Patent number
US05434292

Reaction notes

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