Reaktion #56336

Reaktionsgleichung

1-(2'-methylphenyl)-3-methylamidinourea hydrochloride

NH4OH

N,N-dimethylformamide dimethylacetal

CH3CN

CH3CN

→

1-(2'-methylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one

Lösungsmittel

CHCl3 H2O

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONTo a magnetically stirred suspension of 9.72 g
2. 2
   workup.ADDITIONAfter the mixture is further diluted with 25 ml
3. 3
   workup.DISSOLUTIONis dissolved
4. 4
   TemperaturThe solution is refluxed for 2 hours
5. 5
   Sonstigeseparated
6. 6
   ExtraktionThe aqueous layer is extracted with CHCl3 (for a total of 3×50 ml
7. 7
   Waschenwashed with H2O (2×50 ml.)
8. 8
   Extraktionback extracted with CHCl3 (1×50 ml.)
9. 9
   Sonstigedried
10. 10
    Filtrationfiltered
11. 11
    Einengenconcentrated in vacuo
12. 12
    Sonstigeto yield the product which
13. 13
    Sonstigeis recrystallized from absolute EtOH
14. 14
    Filtrationfiltered
15. 15
    Waschenwashed with cold absolute EtOH
16. 16
    Sonstigeair-dried

Vorschrift

To a magnetically stirred suspension of 9.72 g. (40 mmol) of 1-(2'-methylphenyl)-3-methylamidinourea hydrochloride in 30 ml. of CH3CN is added 9.52 g. (80 ml.) of N,N-dimethylformamide dimethylacetal. After the mixture is further diluted with 25 ml. CH3CN and stirred for 5 minutes all of the solid is dissolved. TLC (3% NH4OH) shows a new spot; about equal in size to a spot in starting material; (EtoAc/MeOH; 9:1) shows mostly a new spot. The solution is refluxed for 2 hours. The reaction mixture is allowed to cool to ambient temperature. The reaction mixture is then poured into CHCl3 /H2O and separated. The aqueous layer is extracted with CHCl3 (for a total of 3×50 ml.). The organic layers are combined and washed with H2O (2×50 ml.). The aqueous layers are combined and back extracted with CHCl3 (1×50 ml.). All organic layers are combined, dried, filtered and concentrated in vacuo to yield the product which is recrystallized from absolute EtOH, filtered and washed with cold absolute EtOH and air-dried. The product is 1-(2'-methylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one, melting point 191.5°-192.5° C.

Quelle