Potassium Cyanide → HCID 59483859, compound

HRID 1808374Notes

Reaction equation

HRID 1808374 reaction equation
[C-:1]#[N:2].[K+].Br[CH2:5][C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH2:11][N:12]2[S:15]([C:18]2[C:23]([CH3:24])=[CH:22][C:21]([O:25][CH3:26])=[CH:20][C:19]=2[CH3:27])(=[O:17])=[O:16])=[CH:8][CH:7]=1>CO.O.C(OCC)(=O)C>[CH3:26][O:25][C:21]1[CH:22]=[C:23]([CH3:24])[C:18]([S:15]([N:12]2[C:13]3[C:9](=[CH:8][CH:7]=[C:6]([CH2:5][C:1]#[N:2])[CH:14]=3)[CH2:10][CH2:11]2)(=[O:17])=[O:16])=[C:19]([CH3:27])[CH:20]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 59483863HCID 59483863, compound

Product 1

HCID 59483859HCID 59483859, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium cyanide (0.133 g, 0.0020 mol) was added to a solution of 6-(bromomethyl)-1-(4-methoxy-2,6-dimethylphenylsulfonyl)indoline (0.7 g, 0.0017 mol) in methanol (14 ml) and water (2 ml), and the resulting reaction mixture was refluxed for 4 h. The mixture was then diluted with ethyl acetate (400 ml) and washed with saturated sodium chloride solution (2×), water (2×), saturated iron sulfate solution and finally with saturated sodium chloride solution. It was then dried (Na2SO4), filtered and concentrated in vacuo. The resulting crude product was used directly in the following stage. Yield: 0.6 g (99%).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 4 h
  3. washwashed with saturated sodium chloride solution (2×), water (2×), saturated iron sulfate solution and finally with saturated sodium chloride solution
  4. dry with materialIt was then dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05357e864d724e5b9700729a56d61b38
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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