Potassium Cyanide → 5-Cyanomethyl-N-(1,1-dimethylethyl)-2-methoxybenzenesulfonamide

HRID 2232023Notes

Reaction equation

HRID 2232023 reaction equation
[C-:1]#[N:2].[K+].Br[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:20][CH3:21])=[C:10]([S:12]([NH:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])=[O:13])[CH:11]=1>CS(C)=O>[C:1]([CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:20][CH3:21])=[C:10]([S:12]([NH:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])=[O:13])[CH:11]=1)#[N:2]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 139214535-Bromomethyl-N-(1,1-dimethylethyl)-2-methoxybenzenesulfonamide

Product 1

HCID 139214545-Cyanomethyl-N-(1,1-dimethylethyl)-2-methoxybenzenesulfonamideYield 44.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1.63 g potassium cyanide and 8 g of the compound from Example 1 in 50 ml of DMSO was stirred at room temperature overnight. The solution became darker in color with time, going from orange to purple to black. After being stirred overnight the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered and the solvent evaporated. The residual red oil was eluted through a dry silica column with 20% ethyl acetate--80% dichloromethane. The product band was isolated to give 3.0 g solid m.p. 146°-147° C.;

Workup

  1. stirringAfter being stirred overnight the reaction mixture
  2. customwas partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. washThe residual red oil was eluted through a dry silica column with 20% ethyl acetate--80% dichloromethane
  8. customThe product band was isolated

Sources & evidence

ORD record
ord-d60ead78d86845dda1a7eefa883c4c77
Source dataset
uspto-grants-1988_11
Patent number
US04786314

Reaction notes

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