5-Methyl-2-thiophenecarboxaldehyde → HCID 67331876, compound

HRID 1896755Notes

Reaction equation

HRID 1896755 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:13].[CH3:14][C:15]1[S:19][C:18]([CH:20]=O)=[CH:17][CH:16]=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C(O)C>[CH2:11]([S:8]([C:6]1[CH:5]=[CH:4][C:3]2[O:13][C:20]([C:18]3[S:19][C:15]([CH3:14])=[CH:16][CH:17]=3)=[N:1][C:2]=2[CH:7]=1)(=[O:10])=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 616635-Methyl-2-thiophenecarboxaldehydeHCID 6432182-Amino-4-(ethylsulphonyl)phenolHCID 178418268HCID 178418268, compound

Product 1

HCID 67331876HCID 67331876, compoundYield 0.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 2-amino-4-(ethylsulfonyl)phenol (452.7 mg, 2.25 mmol) in ethanol (17 mL) was added 5-methyl-2-thiophenecarboxaldehyde (242 μL, 2.25 mmol). The mixture was heated at 70° C. for 70 min. After cooling, a small amount of precipitate was formed. After filtration and evaporation of the filtrate, the resulting product was dissolved in acetonitrile (9.8 mL) and lead tetraacetate (887 mg, 2 mmol) was added. The resulting mixture was heated at 100° C. for 5 min. After cooling, the reaction mixture was filtered off, and the filtrate evaporated in vacuo. The resulting mixture was purified by column chromatography eluting with ethyl acetate/hexanes 20:80 v/v, and then purified by reverse phase HPLC to afford 2.2 mg (0.3%) of the title product (LCMS RT=6.41 min, MH+ 308.1)

Workup

  1. temperatureAfter cooling
  2. customa small amount of precipitate was formed
  3. filtrationAfter filtration and evaporation of the filtrate
  4. dissolutionthe resulting product was dissolved in acetonitrile (9.8 mL)
  5. temperatureThe resulting mixture was heated at 100° C. for 5 min
  6. temperatureAfter cooling
  7. filtrationthe reaction mixture was filtered off
  8. customthe filtrate evaporated in vacuo
  9. customThe resulting mixture was purified by column chromatography
  10. washeluting with ethyl acetate/hexanes 20:80 v/v
  11. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-68a2bd8ab47f42b9bfd7c00577bba2fe
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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