Hydrochloric Acid → HCID 178420020, compound

HRID 1354410Notes

Reaction equation

HRID 1354410 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[N-:14]=[N+:15]=[N-:16].[Na+].Cl.C(N(CC)CC)C.Cl>O.CN1CCCC1=O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:13]=[CH:12][C:9]([C:10]2[NH:16][N:15]=[N:14][N:11]=2)=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 27784284-(1,3-Dioxolan-2-yl)benzonitrile

Product 1

HCID 178420020HCID 178420020, compoundYield 24.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-(1,3-dioxolan-2-yl)benzonitrile (1.0 g), sodium azide (1.48 g), triethylamine hydrochloride (1.18 g) and 1-methyl-2-pyrrolidinone (50 ml) was stirred at 150° C. for 3 hrs. After cooling, 1 M hydrochloric acid and water were added to the reaction mixture to adjust to pH=3 to 4. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from ethyl acetate to give 5-[4-(1,3-dioxolan-2-yl)phenyl]-1H-tetrazole (0.300 g, yield 24%) as brown prism crystals. melting point: 197–199° C. (decomposition).

Workup

  1. temperatureAfter cooling
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-41c564ea45344a7690b3d0ee8556593d
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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