3-Hydroxybenzaldehyde → HCID 21071548, compound

HRID 1666788Notes

Reaction equation

HRID 1666788 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[OH:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 764302-Bromothiazole

Product 1

HCID 21071548HCID 21071548, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a sealed tube, combine 2-bromo-thiazole (2.0 ml, 22.2 mmol), 3-hydroxy-benzaldehyde (1.8 g, 15.0 mmol) and potassium carbonate (2.1 g, 15.0 mmol) in dimethylformamide (20 ml). Heat to 100° C. After 48 hours, cool, pour into water (150 ml), and extract with ether. Combine the organic layers and wash sequentially with distilled water and brine and then dry, (Na2SO4), filter, and concentrate to give a residue. Chromatograph the residue eluting with 9:1 hexane:EtOAc to give the title compound.

Workup

  1. customIn a sealed tube, combine
  2. temperaturecool
  3. extractionextract with ether
  4. washwash sequentially with distilled water and brine
  5. dry with materialdry, (Na2SO4),
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto give a residue
  9. washChromatograph the residue eluting with 9:1 hexane

Sources & evidence

ORD record
ord-21c297043fa14688a13a5b26129ee70e
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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