Dimethylformamide dimethyl acetal → 1-(2-Methylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one

HRID 2049551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2049551
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]([NH:12][C:13](=[NH:16])[NH:14][CH3:15])=[O:11].[CH3:17]OC(OC)N(C)C.[NH4+].[OH-].CC(O)C.CCOC(C)=O.CO>CC#N.C(Cl)(Cl)Cl.O>[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH:15]=[N:14][C:13]([NH:16][CH3:17])=[N:12][C:10]1=[O:11]

Komponenten

7

Edukt 4

HCID 78373Dimethylformamide dimethyl acetalHCID 21584119Ethylacetate methanolHCID 22611478Ammonium hydroxide isopropanolHCID 178485163HCID 178485163, Verbindung

Produkt 1

HCID 130393701-(2-Methylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittel2×HCID 22418719Chloroform waterLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

  1. dissolutionall of the solid had dissolved
  2. temperatureThe solution was refluxed for two hours
  3. customseparated
  4. extractionThe aqueous layer was extracted with CHCl3 (for a total of 3×50 ml)
  5. washwashed with H2O (2×50 ml)
  6. extractionback-extracted with CHCl3 (1×50 ml)
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto yield the product which
  11. customwas recrystallized from absolute EtOH
  12. filtrationfiltered
  13. washwashed with cold absolute EtOH
  14. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-4ff1a45a3a7e47baac78acf1436d4381
Quelldatensatz
uspto-grants-1980_04
Patentnummer
US04198409

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