Sodium ethoxide → HCID 178439158, compound

HRID 638579Notes

Reaction equation

HRID 638579 reaction equation
[C:1]([C:3]1[C:7](C)=[CH:6][S:5][C:4]=1[N:9]=[CH:10]OCC)#[N:2].[CH3:14][C:15]1[CH:24]=[C:23]([CH2:25][CH2:26][CH3:27])[CH:22]=[C:21]([CH3:28])[C:16]=1[O:17][CH2:18][CH2:19][NH2:20].[O-][CH2:30]C.[Na+]>C(O)C>[CH3:14][C:15]1[CH:24]=[C:23]([CH2:25][CH2:26][CH3:27])[CH:22]=[C:21]([CH3:28])[C:16]=1[O:17][CH2:18][CH2:19][NH:20][C:1]1[N:2]([CH3:30])[CH2:10][N:9]=[C:4]2[S:5][CH:6]=[CH:7][C:3]=12

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 20252702HCID 20252702, compoundHCID 54343475HCID 54343475, compound

Product 1

HCID 178439158HCID 178439158, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3.9 g (0.02 mole) of 3-cyano-2-ethoxymethyleneamino-4-methylthiophene and 4.1 g (0.02 mole) of 2-(2,6-dimethyl-4-propylphenoxy)ethylamine were dissolved in 30 ml of ethanol, and the solution was heated under reflux for 5 hours. It was then cooled and 50 ml of ethanol containing 0.05 mole of sodium ethoxide were added; the whole mixture was then heated under reflux for 6 hours. At the end of this time, the ethanol was distilled off and water was added to the residue. The oily phase was separated and extracted with benzene. The benzene extract was washed with water and dried over anhydrous sodium sulphate, after which the solvent was distilled off and the residue was subjected to column chromatography through silica gel eluted with a 9:1 by volume mixture of benzene and ethyl acetate, to give 4.2 g (yield 59%) of the desired Compound No. 16 in the form of colourless crystals melting at 86°-88° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 5 hours
  3. temperatureIt was then cooled
  4. temperaturethe whole mixture was then heated
  5. temperatureunder reflux for 6 hours
  6. distillationAt the end of this time, the ethanol was distilled off
  7. additionwater was added to the residue
  8. customThe oily phase was separated
  9. extractionextracted with benzene
  10. extractionThe benzene extract
  11. washwas washed with water
  12. dry with materialdried over anhydrous sodium sulphate
  13. distillationafter which the solvent was distilled off
  14. washeluted with a 9:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-ddce97d3f29e461a9343c8d4f1287315
Source dataset
uspto-grants-1985_12
Patent number
US04562193

Reaction notes

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