Benzaldehyde → Ethyl 2-benzylideneaminobutyrate

HRID 398809

Reaction equation

HRID 398809 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 dichioromethane (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-3c5cb32813c44d02b95d64edcf9341ec
Source dataset
uspto-grants-1998_10
Patent number
US05817652

Linked notes

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