Ethanol → HCID 16773539, compound

HRID 2243436Notes

Reaction equation

HRID 2243436 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])=[CH:6][C:5]=1[CH3:18])([O-])=O.CCO.C(OCC)(=O)C>[Pd].C(O)(=O)C>[NH2:1][C:4]1[CH:17]=[CH:16][C:7]([C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])=[CH:6][C:5]=1[CH3:18]

Participants

6

Reactant 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 3108186HCID 3108186, compound

Product 1

HCID 16773539HCID 16773539, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

4-Nitro-3-methyl-N-thiazol-2-yl-benzamide (63 mmol) was suspended in abs. EtOH (200 mL) and ethyl acetate (100 mL) and glacial acetic acid (10 mL) was added followed by 10% Pd/C (1 g). The mixture was hydrogenated over night at 3 bar H2. The hydrogenation mixture was filtered and the solvent was removed under reduced pressure. The crude product was added NaHCO3 (sat.) and ethyl acetate, the remaining solid fraction was removed by filtration and dried in vacuo. The liquid phases were separated, the organics were washed with brine, dried over MgSO4, filtered and evaporated to yield the product as a solid.

Workup

  1. waitThe mixture was hydrogenated over night at 3 bar H2
  2. filtrationThe hydrogenation mixture was filtered
  3. customthe solvent was removed under reduced pressure
  4. additionThe crude product was added NaHCO3 (sat.) and ethyl acetate
  5. customthe remaining solid fraction was removed by filtration
  6. customdried in vacuo
  7. customThe liquid phases were separated
  8. washthe organics were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-edc81edea6ac4558aaf295373948b388
Source dataset
uspto-grants-2010_03
Patent number
US07674912B2

Reaction notes

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