4-Chlorobenzaldehyde → HCID 11172159, compound

HRID 743447Notes

Reaction equation

HRID 743447 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.Cl.[CH3:11][O:12][C:13](=[O:17])[CH:14]([CH3:16])[NH2:15].S([O-])([O-])(=O)=O.[Mg+2].C(N(CC)CC)C>C(Cl)Cl>[CH3:11][O:12][C:13](=[O:17])[CH:14]([CH3:16])[N:15]=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 2756298Alanine, methyl ester, hydrochloride (1:1)

Product 1

HCID 11172159HCID 11172159, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring mixture of 4-chlorobenzaldehyde (42.2 g, 0.3 mol), DL-alanine methyl ester hydrochloride (42.7 g, 0.306 mol), and 150 g of magnesium sulfate in 1 L of methylene chloride was added 30.3 g (0.3 mol) of triethylamine in 150 ml of methylene chloride in one portion and the resulting mixture was stirred for 20 hours. The reaction mixture was filtered, the filtrate concentrated in vacuo, and the residue (solid and oil) was dissolved in 500 ml of ether. The insoluble solid (triethylamine hydrochloride) was removed by filtration and the filtrate was concentrated in vacuo to afford 64.01 g (94.6%) of N-(4-chlorophenyl)methylene-DL-alanine methyl ester as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionthe residue (solid and oil) was dissolved in 500 ml of ether
  4. customThe insoluble solid (triethylamine hydrochloride) was removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-780fd9cd2efc47468d6090fc91c9641c
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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