Potassium Carbonate → HCID 15005406, compound

HRID 1672538Notes

Reaction equation

HRID 1672538 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=[O:2].[N+:11]([CH:13](S(C1C=CC(C)=CC=1)(=O)=O)[CH3:14])#[C-:12].C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:14][C:13]1[N:11]=[CH:12][O:2][C:1]=1[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660424-CyanobenzaldehydeHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzene

Product 1

HCID 15005406HCID 15005406, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Formylbenzonitrile (1.61 g, 12.3 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (2.58 g, 12.3 mmol), and potassium carbonate (3.39 g, 24.5 mmol) in methanol (60 mL) was heated to reflux overnight. The reaction mixture was cooled and the volatiles evaporated. The residue was partitioned between water and ethyl acetate. The organic phase was washed with water and brine, dried over Na2SO4, filtered, and evaporated. The solid was chromatographed on silica gel, eluting with 10% to 50% ethyl acetate:hexanes to afford 1.70 g (75% yield) of the title compound as a white solid.

Workup

  1. temperatureto reflux overnight
  2. temperatureThe reaction mixture was cooled
  3. customthe volatiles evaporated
  4. customThe residue was partitioned between water and ethyl acetate
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe solid was chromatographed on silica gel
  10. washeluting with 10% to 50% ethyl acetate

Sources & evidence

ORD record
ord-cdc7b9fa79ef48afbf4c574dc0816188
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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