Water → HCID 22319130, compound

HRID 547733Notes

Reaction equation

HRID 547733 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:27])[N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=1)=[O:2].S([CH2:38][N+:39]#[C-:40])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].O>CO>[O:2]1[C:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:9]2[C:10](=[O:27])[N:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:14]=2)=[CH:40][N:39]=[CH:38]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 22319114HCID 22319114, compound

Product 1

HCID 22319130HCID 22319130, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

13 mg of 3-(2-formylphenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one was dissolved in 10 ml of methanol. To the mixture were added 11 mg of tosylmethylisocyanide and 8 mg of potassium carbonate, followed by heating under reflux overnight. After the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. It was filtered through NH silica gel and silica gel, and the filtrate was evaporated. The resulting precipitates were washed with ether and dried, to give 9 mg of the title compound.

Workup

  1. temperatureby heating
  2. temperatureunder reflux overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationIt was filtered through NH silica gel and silica gel
  7. customthe filtrate was evaporated
  8. customThe resulting precipitates
  9. washwere washed with ether
  10. customdried

Sources & evidence

ORD record
ord-71406cf774494a5faf9d74600956ec0d
Source dataset
uspto-grants-2011_05
Patent number
US07939549B2

Reaction notes

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