2,6-Lutidine → 5-Amino-N-(triethylsilyl)-1H-1,2,4-triazole-3-carboxamide

HRID 1931544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1931544
[NH2:1][C:2]1[N:6]=[C:5]([C:7]([NH2:9])=[O:8])[NH:4][N:3]=1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:24]([CH2:29][CH3:30])([CH2:27][CH3:28])[CH2:25][CH3:26])(=O)=O>ClCCCl.C(OCC)(=O)C>[NH2:1][C:2]1[N:6]=[C:5]([C:7]([NH:9][Si:24]([CH2:29][CH3:30])([CH2:27][CH3:28])[CH2:25][CH3:26])=[O:8])[NH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 79372,6-LutidineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 187074943-amino-1H-1,2,4-triazole-5-carboxamide(SALTDATA: FREE)

Produkt 1

HCID 593125935-Amino-N-(triethylsilyl)-1H-1,2,4-triazole-3-carboxamideAusbeute 26,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A stirred mixture of 3-amino-1H-1,2,4-triazole-5-carboxamide (103 mg, 0.810 mol) in 1,2-dichloroethane (1.62 mL) treated at room temperature with 2,6-lutidine (283 μL, 2.43 mmol) and triethylsilyl trifluoromethanesulfonate (458 μL, 2.03 mmol). After 22 hours the reaction was heated at 50° C. and after 1.5 hours of heating the reaction was allowed to cool to room temperature. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (25 mL), dried over magnesium sulfate, filtered, and evaporated to an oil which was flash chromatographed (silica gel, 0-10% ethyl acetate:hexane) to give the title compound as a white solid (130 mg).

Aufarbeitung

  1. temperatureof heating the reaction
  2. temperatureto cool to room temperature
  3. washwashed with water (25 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil which
  7. customchromatographed (silica gel, 0-10% ethyl acetate:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-5fb4753ee4434cab8649ff79e66580bc
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188085B2

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