Reaktion #323177

Reaktionsgleichung

4-chlorobenzylamine

2-(methylthio)-2-imidazoline hydroiodide

sodium ethoxide

2-[(4-chlorophenyl)methyl]amino-2-imidazoline

ethyl oximinocyanoacetate

→

pink powder

Ausbeute 77.0%

7-Amino-2,3-Dihydro-8-[(4-Chlorophenyl)Methyl]-6-Nitrosoimidazo[1,2-a]Pyrimidin-5(8H)-One

Ausbeute 77.0%

Lösungsmittel

EtOH

ethanol

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is heated
2. 2
   Sonstigeto boiling on a steam bath in an open flask
3. 3
   TemperaturThe bright yellow solution is refluxed for 3 hr
4. 4
   SonstigeThe yellow precipitate is collected
5. 5
   Waschenwashed with i-PrOH
6. 6
   Sonstigepartially air-dried
7. 7
   workup.DISSOLUTIONThe damp sodium salt is dissolved in 2000 ml H2O
8. 8
   FiltrationThe bright pink precipitate is filtered
9. 9
   Sonstigeaid-dried overnight
10. 10
    Sonstigeoven-dried in vacuo at 100°

Vorschrift

To a solution of 62.30 g. 0.44 mol) of 4-chlorobenzylamine in 500 ml absolute EtOH (dried over 4A molecular sieve aluminosilicate desiccant) is added 107.40 g (0.44 mol) 2-(methylthio)-2-imidazoline hydroiodide. The mixture is heated to boiling on a steam bath in an open flask and about 150 ml of the ethanol is allowed to slowly boil off over 2 hr. This solution is added while still hot to 1.76 mole of sodium ethoxide in 1650 ml absolute EtOH. To the resulting stirred, basic solution of 2-[(4-chlorophenyl)methyl]amino-2-imidazoline is then added 61.85 g (0.44 mol) crystalline (mp 129°-131°) ethyl oximinocyanoacetate in portions. The bright yellow solution is refluxed for 3 hr and then cooled to room temperature. The yellow precipitate is collected, washed with i-PrOH, and partially air-dried. The damp sodium salt is dissolved in 2000 ml H2O and acidified with glacial HOAc. The bright pink precipitate is filtered and aid-dried overnight, then oven-dried in vacuo at 100° to yield 103.05 g (77%) of pink powder, mp 238°-241°d. Recrystallization of this material from DMF-EtOH gives red crystals, mp 241°d.

Quelle