Benzaldehyde → Diethyl 2-(benzylideneamino)2-methylnonanedioate

HRID 444052Notes

Reaction equation

HRID 444052 reaction equation
[NH2:1][CH:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:27]I>C1C=CC=CC=1>[CH:19](=[N:1][C:2]([CH3:27])([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 6328Methyl iodideHCID 6455180Diethyl 2-aminononane-1,9-dioate

Product 1

HCID 12783288Diethyl 2-(benzylideneamino)2-methylnonanedioateYield 91.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Diethyl 2-aminononanedioate (5.0 g) was heated with benzaldehyde (2.15 g) in benzene (10 ml) under reflux for 12/3 hours, removing the water formed by means of a Dean and Stark apparatus. The benzene was evaporated in vacuo and the residual oil was taken up in dry tetrahydrofuran (20 ml), stirred under dry nitrogen, treated with sodium hydride (0.61 g of a 80% dispersion in mineral oil), and heated until evolution of hydrogen began. Thereafter, reaction was allowed to proceed at room temperature. When effervescence had ceased, the pale yellow-brown solution was cooled in ice-water and, with continued stirring, treated with methyl iodide (6.83 g); the cooling bath was removed after 15 minutes and the mixture was set aside at room temperature overnight. The resulting suspension of solid was diluted with ether (100 ml) and shaken with ice-cold water (100 ml), and the ethereal phase was washed with H2O, dried over sodium sulphate, and evaporated, to leave crude diethyl 2-(benzylideneamino)2-methylnonanedioate (6.4 g) as a yellow oil.

Workup

  1. temperatureunder reflux for 12/3 hours
  2. customremoving the water
  3. customformed by means of a Dean and Stark apparatus
  4. customThe benzene was evaporated in vacuo
  5. additiontreated with sodium hydride (0.61 g of a 80% dispersion in mineral oil), and
  6. temperatureheated until evolution of hydrogen
  7. customThereafter, reaction
  8. customto proceed at room temperature
  9. customthe cooling bath was removed after 15 minutes
  10. additionThe resulting suspension of solid
  11. additionwas diluted with ether (100 ml)
  12. stirringshaken with ice-cold water (100 ml)
  13. washthe ethereal phase was washed with H2O
  14. dry with materialdried over sodium sulphate
  15. customevaporated

Sources & evidence

ORD record
ord-ae4d5833fcd44617b08508306ad8e828
Source dataset
uspto-grants-1981_04
Patent number
US04262128

Reaction notes

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