Sulfuric Acid → 5-(4-iodo-1-methyl-1H-pyrazol-5-yl)-2H-tetrazole

HRID 588379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588379
[I:1][C:2]1[CH:3]=[N:4][N:5]([CH3:9])[C:6]=1[C:7]#[N:8].[N-:10]=[N+:11]=[N-:12].[Na+].[Cl-].[NH4+].N([O-])=O.[Na+].OS(O)(=O)=O>O.CN(C=O)C>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH3:9])[C:6]=1[C:7]1[N:10]=[N:11][NH:12][N:8]=1

Komponenten

8

Edukt 5

HCID 1118Sulfuric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 601366314-Iodo-1-methyl-1H-pyrazole-5-carbonitrile

Produkt 1

HCID 1176528035-(4-iodo-1-methyl-1H-pyrazol-5-yl)-2H-tetrazoleAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A reaction vessel was charged with DMF (1.225 L), Preparation 21, 4-iodo-1-methyl-1H-pyrazole-5-carbonitrile (175 g, 751 mmol), sodium azide (147 g, 2.25 mol), and ammonium chloride (121 g, 2.25 mol). H2O (525 mL) was added slowly to minimize exotherm. The reaction mixture was heated at 100° C. overnight. The reaction mixture was cooled to room temperature and poured into a mixture of H2O (2 L) and ice (1 kg). An aqueous solution of NaNO2 (600 mL, 120 g NaNO2, 20% by weight) was added followed by the slow addition of aqueous H2SO4 until the pH of the reaction mixture was 1. The precipitate was collected via filtration, washed with H2O and dried in vacuo to afford 5-(4-iodo-1-methyl-1H-pyrazol-5-yl)-2H-tetrazole as a colorless solid (187 g, 90%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe precipitate was collected via filtration
  3. washwashed with H2O
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f442852da50b44c0bbe2640aea6e9147
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227956B2

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