Potassium Carbonate → HCID 68289577, compound

HRID 68760Notes

Reaction equation

HRID 68760 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][CH:5]=1.[N+:13]([CH:15](S(C1C=CC(C)=CC=1)(=O)=O)[CH3:16])#[C-:14].C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][CH:14]=[N:13][C:15]=2[CH3:16])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15294Methyl 4-FormylbenzoateHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzene

Product 1

HCID 68289577HCID 68289577, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-formyl-benzoic acid methyl ester (2.50 g), 1-(1-isocyano-ethanesulfonyl)-4-methyl-benzene (3.19 g), and potassium carbonate (2.76 g) in methanol (50 mL) is heated to reflux for 2 h. After cooling to room temperature, the mixture is poured onto water and extracted with dichloromethane. The organic phase is washed with water, dried over Na2SO4 and concentrated in vacuo. The residue is chromatographed on silica gel (dichloromethane/methanol 40:1) to afford the title compound. LC (method 6): tR=2.68 min; Mass spectrum (ESI+): m/z=218 [M+H]+.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 2 h
  3. additionthe mixture is poured onto water
  4. extractionextracted with dichloromethane
  5. washThe organic phase is washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue is chromatographed on silica gel (dichloromethane/methanol 40:1)

Sources & evidence

ORD record
ord-7479719406c0480abf24392f099b2eff
Source dataset
uspto-grants-2014_09
Patent number
US08822471B2

Reaction notes

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