Water → HCID 72357161, compound

HRID 230439Notes

Reaction equation

HRID 230439 reaction equation
[Cl:1][C:2]1[C:20]([Cl:21])=[CH:19][C:5]2[N:6]([CH2:14][C:15](=O)[CH2:16][CH3:17])[C:7]([CH2:9][C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1.Cl.[NH2:23][OH:24].N1C=CC=CC=1.O>C(O)C>[Cl:1][C:2]1[C:20]([Cl:21])=[CH:19][C:5]2[N:6]([CH2:14][C:15](=[N:23][OH:24])[CH2:16][CH3:17])[C:7]([CH2:9][C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 44430223HCID 44430223, compound

Product 1

HCID 72357161HCID 72357161, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[5,6-Dichloro-2-(2,2,2-trifluoro-ethyl)-benzoimidazol-1-yl]-butan-2-one (339 mg, 1 mmol), hydroxylamine hydrochloride (227.5 mg, 3.25 mmol) and pyridine (3 mL) in ethanol (3 mL) were heated to 70° C. for 5 hours. The reaction mixture was then poured into water and extracted with EtOAc. The organic layer was washed with 15% NaCl, brine, then dried over anhydrous MgSO4. The solvent was distilled out under reduced pressure. Column chromatography (silica gel, EtOAc/hexanes (0% to 60%) yielded the title compound as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with 15% NaCl, brine
  3. dry with materialdried over anhydrous MgSO4
  4. distillationThe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-6c8dda47a51440ef9261c60a3e7b0f6d
Source dataset
uspto-grants-2009_07
Patent number
US07566733B2

Reaction notes

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