Hydrochloric Acid → HCID 178519511, compound

HRID 1040405Notes

Reaction equation

HRID 1040405 reaction equation
[C:1]1([C:7]2[NH:11][N:10]=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])(CC)C.CN(C)[CH:19]=[O:20].Cl>O1CCCC1.C(OCC)(=O)C>[NH:8]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=2[CH:19]=[O:20])=[N:11][N:10]=[N:9]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 178418369HCID 178418369, compoundHCID 178418400CID 53628100

Product 1

HCID 178519511HCID 178519511, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-phenyl-1H-tetrazole (500 mg, 3.42 mmol) in 10 mL of dry tetrahydrofuran was added dropwise s-butyllithium (1.04 mol/L, 6.6 mL, 6.9 mmol) under nitrogen at −78° C. After the reaction mixture was stirred at the same temperature for 30 min, N,N-dimethylformamide (2 mL, 30 mmol) was added dropwise. After the reaction mixture was stirred at room temperature for 10 min, 1M HCl (10 mL) was added. The solution was allowed to warm up to room temperature, diluted with ethyl acetate, and extracted. The extract was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by recrystallization (hexane 2.5 mL, ethyl acetate 2.5 mL) to obtain the title compound (390 mg, 99%).

Workup

  1. stirringAfter the reaction mixture was stirred at room temperature for 10 min
  2. extractionextracted
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customthe residue was purified by recrystallization (hexane 2.5 mL, ethyl acetate 2.5 mL)

Sources & evidence

ORD record
ord-d2bcd3b768784ec9abcb561f7a262b0a
Source dataset
uspto-grants-2013_10
Patent number
US08552220B2

Reaction notes

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