Water → HCID 58495697, compound

HRID 1191056Notes

Reaction equation

HRID 1191056 reaction equation
[CH:1]1([S:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH2:16].[OH:17]OS([O-])=O.[K+]>CC(C)=O>[CH:1]1([S:7]([C:8]2[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=2)(=[O:17])=[O:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 58495647HCID 58495647, compound

Product 1

HCID 58495697HCID 58495697, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve 4-cyclohexylthio-benzonitrile (1.17 g, 5.4 mmol) in acetone (10 mL) and add water until the sulfide starts to come out of solution. Then add a drop of acetone to rehomogenize the solution. Cool the mixture to 0° C. and then add oxone (4.2 g, 6.73 mmol) in one portion while stirring vigorously at 0° C. for h. Concentrate in vacuo, take up the residue in DCM and filter the suspension through a frit. Concentrate in vacuo to obtain the desired intermediate (1.27 g, 94%) as a white solid.

Workup

  1. concentrationConcentrate in vacuo
  2. filtrationfilter the suspension through a frit
  3. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-50e5346b5b4a499e8d1f91ae7e2f8546
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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