Acetic Acid → HCID 62679045, compound

HRID 2243438Notes

Reaction equation

HRID 2243438 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[F:18])([O-])=O.C(O)(=O)C>CCO.C(OCC)(=O)C.[Pd]>[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[F:18]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 62681258HCID 62681258, compound

Product 1

HCID 62679045HCID 62679045, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Nitro-3-fluoro-N-thiazol-2-yl-benzamide (7.5 mmol) was suspended in EtOH (abs., 60 mL) and ethyl acetate (30 mL), glacial acetic acid (5 mL) and 10% Pd/C (300 mg) was added, and the mixture was hydrogenated for 12 days under 3 bar H2. The reaction mixture was filtered and evaporated, and re-dissolved in ethyl acetate (100 mL) and NaHCO3 (sat., 60 mL). The aqueous phase was adjusted to basic pH with NaOH (1M) and the phases were separated. The organic phase was washed with brine, dried over MgSO4, filtered and evaporated.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. dissolutionre-dissolved in ethyl acetate (100 mL)
  4. customthe phases were separated
  5. washThe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-d19a9074ffcf48d4af17eb08df3b0768
Source dataset
uspto-grants-2010_03
Patent number
US07674912B2

Reaction notes

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