1,1'-Carbonyldiimidazole → HCID 44542182, compound

HRID 1785602Notes

Reaction equation

HRID 1785602 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][CH:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=2)[CH2:13][NH2:14])=[CH:5][CH:4]=1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=3)[CH2:13][NH:14][C:23]2=[O:24])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 44542031HCID 44542031, compound

Product 1

HCID 44542182HCID 44542182, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N1-[2-(4-methoxyphenyl)ethyl]-1-(3,4-dimethylphenyl)-1,2-ethanediamine (10.6 g, 0.0356 mol) in dry DMF (55 mL) is added 1,1′-carbonyldiimidazole (6.4 g, 0.0395 mol). The reaction is stirred at 50° C. for 30 minutes, cooled, diluted with ethyl acetate (300 mL), and washed with 0.5 N HCl and brine. The organic phase is dried (MgSO4), and concentrated. The residue is re-crystallized from ethyl acetate (70 mL) to afford 7.5 g (65% yield) of the desired compound. 1H NMR (CDCl3) δ 7.16 (d, J=7.8 Hz, 2H), 7.05 (m, 4H), 6.84 (d, J=7.8 Hz, 2H), 4.50 (t, J=8.1 Hz, 1H), 3.82 (s, 3H), 3.73-3.65 (m, 2H), 3.27 (t, J=8.4 Hz, 1H), 2.91 (m, 1H), 2.78 (m, 1H), 2.68 (m, 1H), 2.30 (s, 6H). MS 325 (MH+). Anal. Calcd. For C20H24N2O2¼H2O: C, 73.03; H, 7.51; N, 8.52. Found: C, 73.29; H, 7.19; N, 8.32.

Workup

  1. temperaturecooled
  2. washwashed with 0.5 N HCl and brine
  3. dry with materialThe organic phase is dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is re-crystallized from ethyl acetate (70 mL)

Sources & evidence

ORD record
ord-cfc1e953b76e4abc85d8c0c35448e1c9
Source dataset
uspto-grants-2009_03
Patent number
US07504517B2

Reaction notes

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