Water → HCID 22953624, compound

HRID 2212063Notes

Reaction equation

HRID 2212063 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].C(=O)([O-])[O-:10].[K+].[K+].I[CH:16]([CH3:18])[CH3:17].[OH2:19]>C(#N)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([CH:16]([CH3:18])[CH3:17])(=[O:10])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 87122-ThiocresolHCID 11430Potassium Carbonate

Product 1

HCID 22953624HCID 22953624, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-methylbenzenethiol (2.37 ml, 20 mmol), potassium carbonate (6.91 g, 50 mmol) and 2-iodopropane (6.00 ml, 60 mmol) in acetonitrile (20 ml) was stirred at 60° C. for 3 days. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was dissolved in methanol (10 ml) and water (2 ml), treated with Oxone™ (18.51 g, 30 mmol) and stirred at room temperature for 3 hours. The mixture was concentrated in vacuo and the residue partitioned between ethyl acetate and water. The organic layer was dried (MgSO4) and concentrated in vacuo to give the title compound (3.44 g, 87%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in methanol (10 ml)
  5. additionwater (2 ml), treated with Oxone™ (18.51 g, 30 mmol)
  6. stirringstirred at room temperature for 3 hours
  7. concentrationThe mixture was concentrated in vacuo
  8. customthe residue partitioned between ethyl acetate and water
  9. dry with materialThe organic layer was dried (MgSO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-caf8945ecf5f4b4e9016997a6d1bb34b
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

Loading…