Reaktion #725761

Reaktionsgleichung

sodium ethoxide

3-cyano-2-ethoxymethyleneamino-4-methylthiophene

2-(2,6-dimethyl-4-propylphenoxy)ethylamine

→

desired Compound

Ausbeute 59.0%

4-[2-(2,6-dimethyl-4-propylphenoxy)ethylamino]-3-methylthieno[2,3-d]pyrimidine

Ausbeute 59.0%

Lösungsmittel

ethanol

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe solution was heated
2. 2
   Temperaturunder reflux for 5 hours
3. 3
   TemperaturIt was then cooled
4. 4
   Temperaturthe whole mixture was then heated
5. 5
   Temperaturunder reflux for 6 hours
6. 6
   workup.DISTILLATIONAt the end of this time, the ethanol was distilled off
7. 7
   workup.ADDITIONwater was added to the residue
8. 8
   SonstigeThe oily phase was separated
9. 9
   Extraktionextracted with benzene
10. 10
    ExtraktionThe benzene extract
11. 11
    Waschenwas washed with water
12. 12
    Trocknendried over anhydrous sodium sulphate
13. 13
    workup.DISTILLATIONafter which the solvent was distilled off
14. 14
    Wascheneluted with a 9:1 by volume mixture of benzene and ethyl acetate

Vorschrift

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.

Quelle