Water → HCID 21094315, compound

HRID 1350079Notes

Reaction equation

HRID 1350079 reaction equation
[C-:1]#[N:2].[K+].[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][CH:9]2[CH2:23]OS(C)(=O)=O.O>CS(C)=O>[C:1]([CH2:23][CH:9]1[C:8]2[C:13](=[CH:14][CH:15]=[C:6]([O:5][CH3:4])[CH:7]=2)[CH2:12][N:11]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:10]1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 21094318HCID 21094318, compound

Product 1

HCID 21094315HCID 21094315, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
80 °C

Procedure

Potassium cyanide (5.52 g; 85 mmol) is suspended in 50 ml of DMSO and the solution is heated to 80° C. The compound obtained in Step H (6.3 g; 17 mmol), dissolved beforehand in 50 ml of DMSO, is progressively added to the preceding solution, and then the reaction mixture is heated again at 80° C. for 30 minutes. The solution is poured into 150 ml of water and extracted three times with dichloromethane. The organic phase is then dried over magnesium sulphate, filtered and evaporated. The dark red oil obtained is purified by chromatography on silica gel (eluant:cyclohexane with the progressive addition of ethyl acetate until the proportions 8/2 are reached) and the solid obtained is recrystallised from cyclohexane to yield the title product in the form of a white solid.

Workup

  1. additionis progressively added to the preceding solution
  2. temperaturethe reaction mixture is heated again at 80° C. for 30 minutes
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe organic phase is then dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe dark red oil obtained
  8. customis purified by chromatography on silica gel (eluant
  9. additioncyclohexane with the progressive addition of ethyl acetate until the proportions 8/2
  10. customobtained
  11. customis recrystallised from cyclohexane

Sources & evidence

ORD record
ord-c27813e2a04b43ec9a69e6dc92c28eac
Source dataset
uspto-grants-2007_05
Patent number
US07214689B2

Reaction notes

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