Benzaldehyde → (E)-tert-butyl 2-(benzylideneamino)acetate

HRID 464239Notes

Reaction equation

HRID 464239 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.S([O-])([O-])(=O)=O.[Mg+2]>C1C=CC=CC=1>[CH:10](=[N:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 151417Glycine tert-butyl ester

Product 1

HCID 14506168(E)-tert-butyl 2-(benzylideneamino)acetateYield 86.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 33.61 gms of glycine t-butyl ester and 27.19 gms of benzaldehyde in 215 ml benzene was added 21.5 gms of magnesium sulfate in one portion with stirring at room temperature. The reaction was stirred 18 hours at room temperature, filtered, diluted with ether and washed with saturated sodium bicarbonate and brine. The ether solution was then dried over magnesium sulfate, concentrated and distilled to yield 48.41 gms (86%) of t-butyl N-benzylideneglycinate.

Workup

  1. stirringThe reaction was stirred 18 hours at room temperature
  2. filtrationfiltered
  3. additiondiluted with ether
  4. washwashed with saturated sodium bicarbonate and brine
  5. dry with materialThe ether solution was then dried over magnesium sulfate
  6. concentrationconcentrated
  7. distillationdistilled

Sources & evidence

ORD record
ord-8dd255ce416b480aa360bcdfc69b2177
Source dataset
uspto-grants-1985_10
Patent number
US04547371

Reaction notes

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