Sulfuric acid magnesium salt (1:1) → HCID 11436703, compound

HRID 505361Notes

Reaction equation

HRID 505361 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].[O-]S([O-])(=O)=O.[Mg+2].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:17]=1[CH:18]=O>C(Cl)(Cl)Cl>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:17]=1[CH:18]=[N:5][CH2:4][CH:3]([O:6][CH3:7])[O:2][CH3:1]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 667262,5-DimethoxybenzaldehydeHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 11436703HCID 11436703, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Aminoacetaldehyde dimethylacetal (20.0 mL, 19.5 g, 0.185 mol) was dissolved in chloroform (100 mL) and MgSO4 (10 g) was added. Then 2,5-dimethoxybenzaldehyde (10d, 7.00 g, 0.042 mol) was also added and the mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with chloroform (100 mL), washed with water (2×200 mL), brine (200 mL), dried (Na2SO4), and concentrated to provide the pure imine as a yellow oil (10.64 g, 100%). 1H NMR (300 MHz CDCl3) 8.66 (s, 1H), 7.47 (d, J=3.0 Hz, 1H), 6.91 (dd, J1=9.0 Hz, J2=3.0 Hz, 1H), 6.81 (d, J=9.0 Hz, 1H), 4.65 (t, J=5.1 Hz, 1H), 3.78 (s, 3H), 3.77 (s, 3H), 3.76 (dd, J1=5.4 Hz, J2=1.2 Hz, 2H), 3.38 (s, 6H).

Workup

  1. washwashed with water (2×200 mL), brine (200 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c4e82b357929409999631fe6994bc6fe
Source dataset
uspto-grants-2010_08
Patent number
US07781445B2

Reaction notes

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