Potassium Carbonate → HCID 68663964, compound

HRID 452796Notes

Reaction equation

HRID 452796 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([CH:15]=[O:16])[C:11]=3[CH:17]=2)=[N:4][N:3]=1.C1(C)C=CC(S([CH2:27][N+:28]#[C-:29])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[O:16][CH:29]=[N:28][CH:27]=4)[C:11]=3[CH:17]=2)=[N:4][N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 86640047HCID 86640047, compound

Product 1

HCID 68663964HCID 68663964, compoundYield 20.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 5-(5-methyl-1,3,4-oxadiazol-2-yl)-1-benzofuran-3-carbaldehyde (500 mg, 2.19 mmol), p-toluenesulfonylmethyl isocyanide (471 mg, 2.41 mmol) and potassium carbonate (363 mg, 2.63 mmol) in methanol (10 mL) was heated under reflux for 7 hr. After cooling, the reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (tetrahydrofuran) and recrystallized from methanol to give the title compound (118 mg, yield 20%) as colorless crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 7 hr
  3. temperatureAfter cooling
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (tetrahydrofuran)
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-97c34b088e6048faaa6e357ae2d79416
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

Loading…