Tetrapropylammonium → 4-(3-(4-tert-Butylphenyl)-2-oxoimidazolidin-1-yl)benzaldehyde

HRID 1710335Notes

Reaction equation

HRID 1710335 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][OH:23])=[CH:18][CH:17]=3)[C:12]2=[O:24])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CCOCC1.C([N+](CCC)(CCC)CCC)CC>C(#N)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:15][CH2:14][N:13]([C:16]3[CH:17]=[CH:18][C:19]([CH:22]=[O:23])=[CH:20][CH:21]=3)[C:12]2=[O:24])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 9559TetrapropylammoniumHCID 82029Methyl morpholine oxideHCID 594568851-(4-tert-Butylphenyl)-3-(4-(hydroxymethyl)phenyl)imidazolidin-2-one

Product 1

HCID 594568184-(3-(4-tert-Butylphenyl)-2-oxoimidazolidin-1-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(4-tert-butylphenyl)-3-(4-(hydroxymethyl)phenyl)imidazolidin-2-one (100 mg, 0.31 mmol), 4-methylmorpholine N-oxide (72 mg, 0.62 mmol), and 4 A molecular sieves (100 mg) in 10 ml of acetonitrile was treated with tetrapropylammonium perruthnate and the resulting mixture was stirred at room temperature for 3 hours. The solids were filtered and the filtrated was concentrated. The residue was purified on ISCO system (2% methanol in dichloromethane) to give a pure product as a white crystalline (72 mg, 73%): 1H NMR (400 MHz, CDCl3) δ 9.93 (s, 1H), 7.81 (d, 2H), 7.79 (d, 2H), 7.50 (d, 2H), 7.40 (d, 2H), 4.03 (s, 4H), 1.33 (s, 9H). MS (ESI) m/z: Calculated: 322.17; Observed: 323.1 (M++1).

Workup

  1. filtrationThe solids were filtered
  2. concentrationthe filtrated was concentrated
  3. customThe residue was purified on ISCO system (2% methanol in dichloromethane)
  4. customto give a pure product as a white crystalline (72 mg, 73%)

Sources & evidence

ORD record
ord-7e0ec03df734456c9f3d96305423e8bd
Source dataset
uspto-grants-2010_09
Patent number
US07790707B2

Reaction notes

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