Hydroxyamine hydrochloride → HCID 86694706, compound

HRID 475147Notes

Reaction equation

HRID 475147 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:17](=O)[CH3:18])[C:5]2[N:9]=[CH:8][N:7](C3CCCCO3)[C:6]=2[CH:16]=1.CC([O-])=O.[Na+].Cl.[NH2:26][OH:27]>CO>[F:1][C:2]1[CH:3]=[C:4]([C:17](=[N:26][OH:27])[CH3:18])[C:5]2[N:9]=[CH:8][NH:7][C:6]=2[CH:16]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 71272278HCID 71272278, compound

Product 1

HCID 86694706HCID 86694706, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-4-yl)ethanone (676 mg, 3.8 mmol), NaOAc (3.12 g, 38 mmol), and hydroxylamine hydrochloride (792 mg, 11.4 mmol) in MeOH (60 mL) was heated at 80° C. for 1 h. The reaction mixture was concentrated in vacuo. To the residue was added water (200 mL) and the resulting mixture was extracted with EOAc (50 mL×3). The combined extracts were concentrated in vacuo to afford 1-(6-fluoro-1H-benzo[d]imidazol-4-yl)ethanone oxime as a yellow solid (658 mg, 89.8%). MS (ESI): m/z=194.3 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionTo the residue was added water (200 mL)
  3. extractionthe resulting mixture was extracted with EOAc (50 mL×3)
  4. concentrationThe combined extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-cc00fe64ba734ee4b71ee9ca70283fc4
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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