Ethanol → 4-AMINO-N-THIAZOL-2-YL-BENZAMIDE

HRID 2243434Notes

Reaction equation

HRID 2243434 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][CH:5]=1)([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][CH:5]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 2303634-Nitro-N-(1,3-thiazol-2-yl)benzamide

Product 1

HCID 2254704-AMINO-N-THIAZOL-2-YL-BENZAMIDE

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

4-Nitro-N-thiazol-2-yl-benzamide (28 mmol) was suspended in abs. EtOH (400 mL) and ethyl acetate (200 mL) and glacial acetic acid (50 mL) was added followed by 10% Pd/C (0.5 g). The mixture was hydrogenated for 72 h 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 a solid. The solid fractions were combined.

Workup

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

Sources & evidence

ORD record
ord-9a61c3e0078b4a8a971519cfc66ed2a0
Source dataset
uspto-grants-2010_03
Patent number
US07674912B2

Reaction notes

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