Hydroxyamine hydrochloride → HCID 86694697, compound

HRID 475104Notes

Reaction equation

HRID 475104 reaction equation
[CH3:1][C:2]1[C:3]([C:17](=O)[CH3:18])=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][O:11]3)[C:6]=2[CH:16]=1.CC([O-])=O.[Na+].Cl.[NH2:26][OH:27]>CO>[CH3:1][C:2]1[C:3]([C:17](=[N:26][OH:27])[CH3:18])=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][O:11]3)[C:6]=2[CH:16]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 71272657HCID 71272657, compound

Product 1

HCID 86694697HCID 86694697, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 1-(6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)ethanone (1.1 g, 4.3 mmol) and NaOAc (3.5 g, 43 mmol) in MeOH (20 mL) at RT was added hydroxylamine hydrochloride (896 mg, 12.9 mmol). The reaction mixture was stirred at 80° C. for 0.5 h then concentrated in vacuo. Water (200 mL) was added, and the mixture was extracted with EtOAc (50 mL×3), dried (MgSO4), and concentrated in vacuo to afford 1-(6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)ethanone oxime as a yellow solid (1.1 g, 90.2%). MS (ESI): m/z=194.3 [M+1]+.

Workup

  1. concentrationthen concentrated in vacuo
  2. additionWater (200 mL) was added
  3. extractionthe mixture was extracted with EtOAc (50 mL×3)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-020ee82d6c244ff288c2c7b472c14326
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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