Hydrochloric Acid → 5-(5-bromo-1,3,4-thiadiazol-2-yl)-1H-tetrazole

HRID 390366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 390366
[Br:1][C:2]1[S:6][C:5]([C:7]2[N:8]=[N:9][N:10](CC(OCC)=O)[N:11]=2)=[N:4][N:3]=1.BrC1SC(C#N)=NN=1.[N-]=[N+]=[N-].[Na+].Cl>CC(O)C.O.[Zn+2].[Br-].[Br-]>[Br:1][C:2]1[S:6][C:5]([C:7]2[NH:11][N:10]=[N:9][N:8]=2)=[N:4][N:3]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 533885265-Bromo-1,3,4-thiadiazole-2-carbonitrileHCID 59321687Ethyl [5-(5-bromo-1,3,4-thiadiazol-2-yl)-2H-tetrazol-2-yl]acetate

Produkt 1

HCID 1784194815-(5-bromo-1,3,4-thiadiazol-2-yl)-1H-tetrazole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 10421208Zinc bromideKatalysatorHCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Ethyl [5-(5-bromo-1,3,4-thiadiazol-2-yl)-2H-tetrazol-2-yl]acetate To a suspension of 5-bromo-1,3,4-thiadiazole-2-carbonitrile (1 g, 5 mmol) and ZnBr2 (1.1 g, 5 mmol) in i-PrOH (10 mL) and H2O (5 mL) was added NaN3 (0.65 g, 10 mmol) in a sealed tube. The mixture was stirred at 120° C. overnight and then cooled to room temperature. The mixture was adjusted to pH=4 with HCl (2 M) and extracted with EtOAc (3×50 mL). The combined organic layers was dried over Na2SO4, filtered and concentrated in vacuo to afford the crude 5-(5-bromo-1,3,4-thiadiazol-2-yl)-1H-tetrazole.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc (3×50 mL)
  3. dry with materialThe combined organic layers was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f95ab8e2fec447a482c7eae555288bf4
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383643B2

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