Hydrochloric Acid → 5-(5-bromo-1,3,4-thiadiazol-2-yl)-1H-tetrazole
Reaction equation
[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]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 120 °C
Procedure
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.
Workup
- temperaturecooled to room temperature
- extractionextracted with EtOAc (3×50 mL)
- dry with materialThe combined organic layers was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-f95ab8e2fec447a482c7eae555288bf4
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383643B2
Reaction notes
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