Acetonitrile → HCID 118108883, compound

HRID 1508663Notes

Reaction equation

HRID 1508663 reaction equation
[C:1](#N)C.Cl.[CH3:5][O:6][NH2:7].[CH2:8]([N:15]([CH:24]1[CH2:28][CH2:27][O:26][CH:25]1O)[C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O.C(OCC)(=O)C.CCCCCC>[CH2:8]([N:15]([CH:24]([CH2:28][CH2:27][OH:26])[CH:25]=[N:7][O:6][CH3:5])[C:16](=[O:23])[C:17]1[CH:22]=[CH:21][C:20]([CH3:1])=[CH:19][CH:18]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 3

HCID 6342AcetonitrileHCID 521874O-Methylhydroxylamine hydrochlorideHCID 118108756HCID 118108756, compound

Product 1

HCID 118108883HCID 118108883, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.2 mL of acetonitrile, 0.6 mL of water and 0.1 g of O-methylhydroxylamine hydrochloride were added to 0.2 g of N-benzyl-N-(2-hydroxyoxolan-3-yl)benzamide, and the obtained mixture was then stirred at room temperature for 0.5 hours. The reaction mixture was then left at rest for 11 hours. Thereafter, hexane, ethyl acetate and water were added to the reaction mixture, and the water layer was then removed. The organic layer was successively washed with water and a saturated sodium chloride aqueous solution, and was then dried over anhydrous sodium sulfate. After that, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=60/40 to 30/70), so as to obtain 99 mg of N-benzyl-N-(4-hydroxy-1-(methoxyimino)butan-2-yl)-4-methylbenzamide in the form of a colorless oily product.

Workup

  1. waitThe reaction mixture was then left at rest for 11 hours
  2. customthe water layer was then removed
  3. washThe organic layer was successively washed with water
  4. dry with materiala saturated sodium chloride aqueous solution, and was then dried over anhydrous sodium sulfate
  5. distillationAfter that, the solvent was distilled away under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=60/40 to 30/70)

Sources & evidence

ORD record
ord-cd017171021543f99fb57fdb55b6e6fd
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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