Potassium Iodide → HCID 19603789, compound

HRID 1604640Notes

Reaction equation

HRID 1604640 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:12])=[C:8]([CH:11]=1)[CH:9]=O)(=[O:3])[CH3:2].Br[CH2:14][C:15]1[S:16][CH:17]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[N:19]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[C:20]([C:18]1[N:19]=[C:15]([C:14]2[O:12][C:7]3[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH3:2])=[CH:11][C:8]=3[CH:9]=2)[S:16][CH:17]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 30853915-AcetylsalicylaldehydeHCID 196037502-Bromomethyl-4-tert-butylthiazole

Product 1

HCID 19603789HCID 19603789, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-acetyl-2-hydroxybenzaldehyde (1.68 g), 2-bromomethyl-4-tert-butylthiazole, potassium carbonate (1.24 g) and potassium iodide (0.59 g) in N,N-dimethylformamide (10 ml) was stirred at room temperature for 5 hours. The resulting mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. A mixture of the resulting syrup and acetic anhydride in xylene was stirred under reflux for 1 day. After being cooled to room temperature, the reaction mixture was concentrated under reduced -pressure. The resulting syrup was subjected to column chromatography on silica gel and eluted with a mixture of toluene and ethyl acetate. The fractions containing the objective compound were combined and concentrated under reduced pressure to give 4-tert-butyl-2-(5-acetylbenzofuran-2-yl)thiazole (1.83 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionA mixture of the resulting syrup and acetic anhydride in xylene
  6. stirringwas stirred
  7. temperatureunder reflux for 1 day
  8. temperatureAfter being cooled to room temperature
  9. concentrationthe reaction mixture was concentrated under reduced -pressure
  10. washeluted with a mixture of toluene and ethyl acetate
  11. additionThe fractions containing the objective compound
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a043ac8040cc4841a9b73e192cac228a
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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