Benzaldehyde → Ethyl 2-(benzylideneamino)acetate

HRID 1263166

Reaction equation

HRID 1263166 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].S([O-])([O-])(=O)=O.[Mg+2].C(N(CC)CC)C.[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:4]([CH2:3][N:2]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 357745Ethyl 2-(benzylideneamino)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To ethyl glycinate hydrochloride (36.4 g) suspended in 500 ml methylene chloride were added magnesium sulfate (22 g) and triethylamine (72 ml, 52.4 g). Benzaldehyde (27.6 g) was added dropwise at 15°-20° C. with stirring. The mixture was stirred at room temperature for two hours, filtered and stripped. To the residue was added 300 ml diethylether and 150 ml brine. After separation the organic layer was collected, and the aqueous layer was extracted with 100 ml ether. The organic phases were combined, dried (MgSO4), filtered and stripped to yield the title product as a pale yellow oil.

Workup

  1. stirringThe mixture was stirred at room temperature for two hours
  2. filtrationfiltered
  3. additionTo the residue was added 300 ml diethylether and 150 ml brine
  4. customAfter separation the organic layer
  5. customwas collected
  6. extractionthe aqueous layer was extracted with 100 ml ether
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-aa81e46f05784623b13d2ebc3b0c126b
Source dataset
uspto-grants-1984_06
Patent number
US04456467

Linked notes

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