Cyanuric chloride → 1-[(4,6-Dichloro-1,3,5-triazin-2-yl)amino]imidazolidine-2,4-dione

HRID 1507051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1507051
Cl.[NH2:2][N:3]1[CH2:9][C:7](=[O:8])[NH:6][C:4]1=[O:5].[N:10]1[C:17]([Cl:18])=[N:16][C:14](Cl)=[N:13][C:11]=1[Cl:12].C(=O)(O)[O-].[Na+]>C(#N)C>[Cl:12][C:11]1[N:10]=[C:17]([Cl:18])[N:16]=[C:14]([NH:2][N:3]2[CH2:9][C:7](=[O:8])[NH:6][C:4]2=[O:5])[N:13]=1

Komponenten

5

Edukt 3

HCID 7954Cyanuric chlorideHCID 516892Sodium BicarbonateHCID 124729631-Aminohydantoin hydrochloride

Produkt 1

HCID 866980651-[(4,6-Dichloro-1,3,5-triazin-2-yl)amino]imidazolidine-2,4-dioneAusbeute 107,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

An ice-cold suspension of 1-aminohydantoin hydrochloride (457 mg, 3.0 mmol), cyanuric chloride (500 mg, 2.73 mmol) and sodium bicarbonate (505 mg, 6 mmol) in acetonitrile (5 mL) was stirred under an atmosphere of nitrogen for 2 h and then stirred at room temperature for 20 h. The reaction mixture was evaporated to dryness under reduced pressure and the residue was extracted with ethyl acetate and the ethyl acetate was separated and dried (MgSO4). The crude product (770 mg) gave a single spot on thin layer chromatography [silica; CH2Cl2/MeOH (10:1)] and was used in the next step without further purification. 1H NMR (CD3CN): δ=4.11 (s, 2H); 8.71 (s, 1H); 8.85 (s, 1H).

Aufarbeitung

  1. stirringstirred at room temperature for 20 h
  2. customThe reaction mixture was evaporated to dryness under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. customthe ethyl acetate was separated
  5. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-6bad961b66414a30b33003948e22f520
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221799B2

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