Benzaldehyde → HCID 178518082, compound

HRID 1987957Notes

Reaction equation

HRID 1987957 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([N+:16]#[C-:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[O:18]([C:20]#[N:21])[K].[Cl:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.Cl.[NH+]1C=CC=CC=1>CO.O>[CH2:9]([NH:16][C:17]1[CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:27]([C:26]2[CH:28]=[CH:29][C:23]([Cl:22])=[CH:24][CH:25]=2)[C:20](=[O:18])[N:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 78124-ChloroanilineHCID 82558Benzyl isocyanideHCID 21584435Pyridinium hydrochlorideHCID 178418250HCID 178418250, compound

Product 1

HCID 178518082HCID 178518082, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The numbers in the formula are aimed for characterizing NMR-spectra. To a solution of benzaldehyde (1 equiv., 0.85 mmol, 94 μL) and benzylisocyanide (1 equiv., 0.85 mmol, 92 μL) in methanol (0.6 mL) was added KOCN (1 equiv., 0.85 mmol, 68 mg) in H2O (0.3 mL) followed by 4-chloroaniline (1 equiv., 0.85 mmol, 98 mg) and pyridinium hydrochloride (1 equiv., 0.85 mmol). The reaction was stirred at room temperature for 3 days and the precipitate filtered. Work-up and purification afforded (rac)-4-benzylamino-1-(4-chloro-phenyl)-5-phenyl-1,5-dihydro-imidazol-2-one (117 mg, 37%) as an amber solid. δH NMR (CDCl3, 300 MHz) 7.45-7.10 (14H, m, H arom), 5.54 (1H, s, C5H), 5.35 (1H, br signal, NH), 4.71 (1H, dd, J=14.5, 5.6 Hz, CHAHBPh), 4.52 (1H, dd, J=14.5, 4.1 Hz, CHAHBPh); m/z (EI) 378.3 (37%), 377.3 (26), 376.3 (100, M+H+).

Workup

  1. filtrationthe precipitate filtered
  2. custompurification

Sources & evidence

ORD record
ord-59b154acb17a4d738da15f830a3ba811
Source dataset
uspto-grants-2009_06
Patent number
US07553862B2

Reaction notes

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