Benzaldehyde → N-benzoyl-N-phenylhydroxylamine

HRID 1099327Notes

Reaction equation

HRID 1099327 reaction equation
C1CCN2C(=NCCC2)CC1.[CH:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[N:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21]>ClCCl>[OH:21][N:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 11473NitrosobenzeneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 67536N-benzoyl-N-phenylhydroxylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DBU (3.8 mg, 0.025 mmol) was added under argon to a solution of benzaldehyde (106 mg, 1 mmol), nitrosobenzene (107 mg, 1 mmol) and catalyst (1.82 mg, 0.005 mmol) in dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 10 min. The solvent was removed under vacuum, and the residue was purified by flash silica gel column chromatography using hexane and ethyl acetate as the eluents.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was purified by flash silica gel column chromatography

Sources & evidence

ORD record
ord-b329f04e011b4e6b8a6985fc7118fdf4
Source dataset
uspto-grants-2012_03
Patent number
US08143423B2

Reaction notes

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