Dimethyl Sulfoxide → HCID 10035404, compound

HRID 1491830Notes

Reaction equation

HRID 1491830 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N+:8]=1[O-])(=[O:3])[CH3:2].S(OC)(OC)(=O)=O.CS(C)=O.[C-:25]#[N:26].[K+]>O>[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:25]#[N:26])[N:8]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6497Dimethyl SulfateHCID 9032Potassium CyanideHCID 11819636HCID 11819636, compound

Product 1

HCID 10035404HCID 10035404, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(2-acetylaminoethyl)pyridine N-oxide (70.8 g) and dimethyl sulfate (41 ml) was stirred at ambient temperature for 1.5 hours. To the mixture was added dimethylsulfoxide (420 ml) and potassium cyanide (25.6 g) and the mixture was stirred at ambient temperature for 3 hours. To the reaction mixture was added water and extracted with chloroform. The extract layer was dried over magnesium sulfate and evaporated in vacuo to give 2-(2-acetylaminoethyl)-6-cyanopyridine (74.3 g).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 3 hours
  2. extractionextracted with chloroform
  3. dry with materialThe extract layer was dried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-75e5d10eacda4300a46e79ff92f46b1e
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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