Benzaldehyde → HCID 25115946, compound

HRID 1099343Notes

Reaction equation

HRID 1099343 reaction equation
C1CCN2C(=NCCC2)CC1.[CH:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:20][N:21]([CH3:30])[C:22]1[CH:27]=[CH:26][C:25]([N:28]=[O:29])=[CH:24][CH:23]=1>ClCCl>[CH3:20][N:21]([CH3:30])[C:22]1[CH:27]=[CH:26][C:25]([N:28]([OH:29])[C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8749N,N-dimethyl-4-nitrosoanilineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 25115946HCID 25115946, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DBU (15 mg, 0.1 mmol) was added under argon to a solution of benzaldehyde (106 mg, 1 mmol), N,N-dimethyl-4-nitrosobenzenamine (150 mg, 1 mmol) and catalyst (36.4 mg, 0.1 mmol) in dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 60 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-b710a58d6a894aff94d4d644f44eb70f
Source dataset
uspto-grants-2012_03
Patent number
US08143423B2

Reaction notes

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