Benzaldehyde → Ethyl 2-benzylideneaminobutyrate

HRID 849

Reaction equation

HRID 849 reaction equation
Cl.[NH2:2][CH:3]([CH2:9][CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].S([O-])([O-])(=O)=O.[Mg+2].C(N(CC)CC)C.[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[CH:24](=[N:2][CH:3]([CH2:9][CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 12844023Ethyl 2-Aminobutyrate Hydrochloride

Product 1

HCID 10331026Ethyl 2-benzylideneaminobutyrateYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from step (a) (149.6 g), magnesium sulphate (74.3 g), and triethylamine (246 ml) in dichloromethane (1500 ml) was stirred at room temperature under nitrogen and benzaldehyde (94.9 g, Aldrich) was added dropwise. The mixture was stirred at room temperature for 3 hours then filtered. The filtrate was concentrated, triturated in diethyl ether, filtered and concentrated to yield the desired product as a yellow oil (174 g). 1H NMR consistent with the proposed structure.

Workup

  1. filtrationthen filtered
  2. concentrationThe filtrate was concentrated
  3. customtriturated in diethyl ether
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-968da5d345074707bd8ae7f036b4987e
Source dataset
uspto-grants-1998_03
Patent number
US05723458

Linked notes

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