Dimethyl Sulfoxide → HCID 57320502, compound

HRID 1588439Notes

Reaction equation

HRID 1588439 reaction equation
S([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-])(=O)=O.[C-:12]#[N:13].[Na+].[C:15](=[O:18])([O-])[O-:16].[K+].[K+].CS(C)=[O:23]>CO>[C:12]([CH2:6][C@H:7]1[C@H:5]([OH:23])[CH2:11][C@H:10]2[C@@H:8]1[CH2:9][C:15](=[O:18])[O:16]2)#[N:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 11430Potassium CarbonateHCID 85570p-Toluenesulfonate

Product 1

HCID 57320502HCID 57320502, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The tosylate (2) was dissolved in dimethyl sulfoxide and sodium cyanide (3.92 g) was added thereto, and the resultant mixture was stirred at 60° to 70° C. for 2 hours. The reaction mixture was worked up with the conventional procedure to give the crude cyano compound (3). The crude cyano compound (3) was dissolved in methanol, and potassium carbonate (2.76 g) was added thereto, and the resultant mixture was stirred for 15 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was chromatographed on a silicagel column to give the titled compound (4).

Workup

  1. customto give the crude cyano compound (3)
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe obtained residue was chromatographed on a silicagel column

Sources & evidence

ORD record
ord-8c13f5e5dfc2447184172f831d8e1bc5
Source dataset
uspto-grants-1993_06
Patent number
US05221799

Reaction notes

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