Benzaldehyde → HCID 4866663, compound

HRID 1647349Notes

Reaction equation

HRID 1647349 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([CH2:7][CH2:8][S:9][CH3:10])[NH2:6].[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl>[CH3:2][O:3][C:4](=[O:11])[CH:5]([N:6]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:7][CH2:8][S:9][CH3:10]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 11435579L-Methionine, methyl ester, hydrochloride

Product 1

HCID 4866663HCID 4866663, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of methionine methyl ester hydrochloride (3.8 g, 19 mmol) and freshly distilled benzaldehyde (2 g, 19 mmol) in dichloromethane (60 mL) was cooled to 0° C. and magnetically stirred. A solution of triethylamine (1.92 g, 19 mmol) in solution in dichloromethane (30 mL) was added slowly thereto. The resulting solution was allowed to stand overnight at room temperature, with stirring. After removal of the solvent, the residue was taken up in anhydrous diethyl ether, with the insoluble material being filtered off. The filtrate was washed with water (3×30 mL), brine (2×40 mL), dried over sodium sulfate, and concentrated, to provide a crude material which was purified by distillation (bp 144° C., 4 mm) providing methyl-2-(benzylideneamino)-4-(methylthio)butyrate (3.62 g) at a yield of 76%.

Workup

  1. stirringwith stirring
  2. customAfter removal of the solvent
  3. filtrationbeing filtered off
  4. washThe filtrate was washed with water (3×30 mL), brine (2×40 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto provide a crude material which
  8. distillationwas purified by distillation (bp 144° C., 4 mm)

Sources & evidence

ORD record
ord-ca86e6e4081d4a998a2ec3d078989725
Source dataset
uspto-grants-1995_07
Patent number
US05430169

Reaction notes

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