Potassium Cyanide → HCID 19804726, compound

HRID 1682152Notes

Reaction equation

HRID 1682152 reaction equation
Br[CH2:2][C:3]1[C:4]([Cl:17])=[C:5]([CH:10]=[CH:11][C:12]=1[S:13]([CH3:16])(=[O:15])=[O:14])[C:6]([O:8][CH3:9])=[O:7].C1OCCOCCOCCOCCOCCOC1.[C-:36]#[N:37].[K+]>C(#N)C>[Cl:17][C:4]1[C:3]([CH2:2][C:36]#[N:37])=[C:12]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 10969914Methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate

Product 1

HCID 19804726HCID 19804726, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.0 g of methyl 3-bromomethyl-2-chloro-4-methanesulfonylbenzoate was added to a solution of 0.4 g of 18-crown-6 and 1.9 g of potassium cyanide in 50 ml of acetonitrile. The mixture was stireed for 72 hours at room temperature. After filtering off the solid, water was added to the filtrate, and the mixture was extracted with chloroform. After washing the extract with water and drying it, the solvent was distilled off to obtain a crude product. The crude product was purified by short silica gel column chlomatography (eluent: chloroform) to obtain 4.1 g of the desired product. Melting point: 151°-155° C.

Workup

  1. filtrationAfter filtering off the solid, water
  2. additionwas added to the filtrate
  3. extractionthe mixture was extracted with chloroform
  4. washAfter washing the
  5. extractionextract with water
  6. customdrying it
  7. distillationthe solvent was distilled off
  8. customto obtain a crude product
  9. customThe crude product was purified by short silica gel column chlomatography (eluent: chloroform)

Sources & evidence

ORD record
ord-b1398a6de0b24621ae951c4909d7d311
Source dataset
uspto-grants-1992_12
Patent number
US05175299

Reaction notes

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