Triethylamine → N-(4-Methoxybenzylidene)glycine methyl ester

HRID 722446Notes

Reaction equation

HRID 722446 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].C(N(CC)CC)C.[CH:15](=O)[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:7])[CH2:5][N:6]=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 312444-MethoxybenzaldehydeHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 4193973N-(4-Methoxybenzylidene)glycine methyl esterYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 77.46 g (0.617 mol) of glycine methylester hydrochloride in CH2Cl2, 92 ml (0.66 mol) of triethylamine, a solution of 60 g (0.44 mol) of p-anisaldehyde in 50 ml of CH2Cl2 and 40 g of MgSO4 are successively added at 0–5° C. under N2 atmosphere. After stirring for 18 h at r.t. the reaction mixture is filtered through celite and washed with CH2Cl2. The filtrate is concentrated under reduced pressure and then the crude mixture is diluted with AcOEt. The AcOEt solution is filtered again to remove triethylamine hydrochloride and the filtrate diluted with toluene and concentrated under reduced pressure (azeotropic removal of H2O) to give 91.3 g of [(4-methoxy-benzylidene)-amino]-acetic acid methyl ester as light yellow crystals; NMR (C6D6): 3.18 (s, 3H), 3.34 (s, 3H), 4.13 (s, 3H), 6.69 (d, 2H, J=8.56 Hz), 7.70 (d, 2H, J=8.56 Hz), 7.79 (s, 1H).

Workup

  1. filtrationis filtered through celite
  2. washwashed with CH2Cl2
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. additionthe crude mixture is diluted with AcOEt
  5. filtrationThe AcOEt solution is filtered again
  6. customto remove triethylamine hydrochloride
  7. additionthe filtrate diluted with toluene
  8. concentrationconcentrated under reduced pressure (azeotropic removal of H2O)

Sources & evidence

ORD record
ord-68500bfdae52498db5d9c33bfab0e7a5
Source dataset
uspto-grants-2006_11
Patent number
US07138432B1

Reaction notes

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