Potassium Carbonate → 2-((3,5-dimethylisoxazol-4-yl)methyl)-2H-tetrazol-5-amine

HRID 658708

Reaktionsgleichung

Reaktionsgleichung von HRID 658708
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[NH2:6].Cl[CH2:8][C:9]1[C:10]([CH3:15])=[N:11][O:12][C:13]=1[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.ClCCl>[CH3:15][C:10]1[C:9]([CH2:8][N:2]2[N:3]=[N:4][C:5]([NH2:6])=[N:1]2)=[C:13]([CH3:14])[O:12][N:11]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 20467AminotetrazoleHCID 88246Isoxazole, 4-(chloromethyl)-3,5-dimethyl-

Produkt 1

HCID 574224592-((3,5-dimethylisoxazol-4-yl)methyl)-2H-tetrazol-5-amineAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2H-tetrazol-5-amine (1.29 g, 12.5 mmol), 4-(chloromethyl)-3,5-dimethylisoxazole (1.56 mL, 12.5 mmol) and potassium carbonate (1.73 g, 15.5 mmol) in DMF (20 mL) were heated to 80° C. with stirring for 16 hours. The reaction was cooled to room temperature, diluted with dichloromethane (100 mL) and washed consecutively with brine and water. The organics were dried over sodium sulfate and concentrated with rotary evaporation. The crude product was purified by silica gel chromatography (0-10% gradient ethyl acetate/dichloromethane) affording 2-((3,5-dimethylisoxazol-4-yl)methyl)-2H-tetrazol-5-amine as a white crystalline solid (970 mg, 40% yield) MS M+H calculated 195.1, found 195.

Aufarbeitung

  1. washwashed consecutively with brine and water
  2. dry with materialThe organics were dried over sodium sulfate
  3. concentrationconcentrated with rotary evaporation
  4. customThe crude product was purified by silica gel chromatography (0-10% gradient ethyl acetate/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-b692dd97deb14fa1a55faf407fa54f84
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076491B2

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