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Dimethylamine → 4-(3-Buten-1-yl)-6-(dimethylamino)-2-hydrazino-1,3,5-triazine

HRID 1786115
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1786115
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[CH2:10]([Mg]Br)[CH2:11][CH:12]=[CH2:13].C[CH2:17][N:18]([CH:22](C)C)C(C)C.CNC.O.[NH2:29][NH2:30]>C1C=CC=CC=1.O1CCOCC1>[CH2:10]([C:2]1[N:4]=[C:5]([N:18]([CH3:22])[CH3:17])[N:7]=[C:8]([NH:29][NH2:30])[N:1]=1)[CH2:11][CH:12]=[CH2:13]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 674DimethylamineHCID 7954Cyanuric chlorideHCID 24654Hydrazine hydrate (1:1)HCID 81531DiisopropylethylamineHCID 178418797HCID 178418797, Verbindung

Produkt 1

HCID 688481234-(3-Buten-1-yl)-6-(dimethylamino)-2-hydrazino-1,3,5-triazine

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 241BenzeneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cyanuric chloride (1.07 g, 5.80 mmol) in anhydrous benzene (10.7 mL) was added at 0° C. dropwise a solution of 3-butenylmagnesium bromide (0.5M in THF, 12.8 mL, 6.38 mmol). The resulting mixture was stirred at 0° C. for 3 hrs. To the mixture were added 1,4-dioxane (10 mL), DIPEA (1.1 mL), followed by addition of dimethylamine (2.0M in MeOH, 3.2 mL, 6.38 mmol) at 0° C. The mixture was stirred and allowed to warm up to room temperature over 2 hours. Finally to it was added hydrazine hydrate (7.0 mL) at room temperature. The mixture was stirred at room temperature overnight. Then the volatiles were evaporated in vacuo. The residue was purified by HPLC to provide the title compound as a white solid. MH+209.

Aufarbeitung

  1. stirringThe mixture was stirred
  2. temperatureto warm up to room temperature over 2 hours
  3. stirringThe mixture was stirred at room temperature overnight
  4. customThen the volatiles were evaporated in vacuo
  5. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-df1d91d0ebde4ebe867f1af20cecb905
Quelldatensatz
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07507726B2

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