Acetic Acid → HCID 25168775, compound

HRID 1044824Notes

Reaction equation

HRID 1044824 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][CH:16]([O:19][NH2:20])[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[CH:23]([C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[C:28]#[N:29])=O.C(O)(=O)C>CCO>[F:22][C:2]([F:1])([F:21])[O:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([N:13]2[CH2:18][CH2:17][CH:16]([O:19]/[N:20]=[CH:23]/[C:25]3[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=3)[C:28]#[N:29])[CH2:15][CH2:14]2)(=[O:11])=[O:12])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 90670m-FormylbenzonitrileHCID 67118448HCID 67118448, compound

Product 1

HCID 25168775HCID 25168775, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of O-(1-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-yl)hydroxylamine (130 mg, 0.38 mmol), 3-formylbenzonitrile (45 mg, 0.38 mmol) and acetic acid (0.022 ml, 0.38 mmol) in EtOH (4 ml) was stirred for 1 hour and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica (EtOAc/Hexanes 20/80-50/50) and recrystallized from EtOAc/Hexanes to give (E)-3-((1-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-yloxyimino)methyl)benzonitrile (96 mg, 56%, colorless solid, LC: 98%, retention time: 7.94 min (Method A), M/Z: 453.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by column chromatography on silica (EtOAc/Hexanes 20/80-50/50)
  3. customrecrystallized from EtOAc/Hexanes

Sources & evidence

ORD record
ord-7a0937df837444209e1e729337f90021
Source dataset
uspto-grants-2013_10
Patent number
US08563732B2

Reaction notes

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