N,N'-Dimethylethylenediamine → 124639-28-7

HRID 2111946Notes

Reaction equation

HRID 2111946 reaction equation
[CH:1](=O)[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH3:11][NH:12][CH2:13][CH2:14][NH:15][CH3:16].[O-]S([O-])(=O)=O.[Mg+2]>C(O)C>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:1]1[N:15]([CH3:16])[CH2:14][CH2:13][N:12]1[CH3:11]

Participants

5

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 86582-MethoxybenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 4144245124639-28-7Yield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of o-anisaldehyde (9.0 g, 66 mmol) and N,N′-dimethylethylenediamine (7.9 mL, 73 mmol) in ethanol (180 mL) was stirred at r.t. for overnight. MgSO4 (30 g) was added and the mixture was stirred for 20 min. The reaction mixture was filtered and washed with ether. The solvent was removed in vacuo to afford 2-(2-methoxyphenyl)-1,3-dimethylimidazolidine as a light yellow solid, 12 g, yield 88%. 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 2.21 (s, 6H) 2.57-2.72 (m, 2H) 3.34 (d, J=2.75 Hz, 2H) 3.82 (s, 3H) 4.13 (s, 1H) 6.88 (d, J=8.24 Hz, 1H) 7.00 (t, J=7.48 Hz, 1H) 7.25-7.30 (m, 1H) 7.67 (d, J=7.63 Hz, 1H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with ether
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-46efad6ca50340efa39227445f5943a8
Source dataset
uspto-grants-2009_04
Patent number
US07521441B2

Reaction notes

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