Sodium Cyanide → HCID 12241882, compound

HRID 2169195Notes

Reaction equation

HRID 2169195 reaction equation
CS(O[CH2:6][C:7]([CH3:15])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])(=O)=O.[C-:16]#[N:17].[Na+]>CS(C)=O.O>[CH3:8][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:15])[CH2:6][C:16]#[N:17]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 13638465HCID 13638465, compound

Product 1

HCID 12241882HCID 12241882, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

2-Methyl-2-phenylpropyl methanesulfonate (52) (12 g, 52.6 mmol) was stirred in dimethyl sulfoxide (106 ml), sodium cyanide (10.3 g, 210 mmol, Eq: 4) was added and the reaction mixture was heated to 110° C. for 20 hours. The reaction mixture was cooled, diluted with water, extracted three times with ether, washed with ether, water, and brine, and dried over magnesium sulfate. The solvent was removed on a rotary evaporator. Chromatography was conducted (2% to 15% over 20 min on a 40 g silica gel column) to give 3-methyl-3-phenylbutanenitrile (53) as a clear oil (4.8 g, 57%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted three times with ether
  3. washwashed with ether, water, and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed on a rotary evaporator
  6. customover 20 min

Sources & evidence

ORD record
ord-da746cb9b4cc47e48cdcb72309bc13bb
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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