Iodoethane → 2-Ethyl-5-(4-methylphenyl)-1,2,3,4-tetraazole

HRID 902100Notes

Reaction equation

HRID 902100 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[N:10][N:9]=2)=[CH:4][CH:3]=1.I[CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:14]([N:11]1[N:10]=[N:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)=[N:12]1)[CH3:15]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178424083HCID 178424083, compound

Product 1

HCID 207099322-Ethyl-5-(4-methylphenyl)-1,2,3,4-tetraazoleYield 79.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 20.0 grams (0.125 mole) of 5-(4-methylphenyl)-1,2,3,4-tetraazole in 230 mL of acetonitrile was stirred and 48.7 grams (0.312 mole) of iodoethane, followed by 17.3 grams (0.125 mole) of potassium carbonate were added. Upon completion of addition, the reaction mixture was warmed to reflux, where it stirred for two hours. After this time, the reaction mixture was concentrated under reduced pressure to a residue. The residue was taken up in ethyl acetate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using 1:4 ethyl acetate:hexane as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 18.8 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionwere added
  2. additionUpon completion of addition
  3. temperaturethe reaction mixture was warmed
  4. temperatureto reflux
  5. concentrationAfter this time, the reaction mixture was concentrated under reduced pressure to a residue
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure to a residue
  8. customThe residue was purified with column chromatography on silica gel using 1:4 ethyl acetate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0666244082ed4466ad614d2b2292ccd8
Source dataset
uspto-grants-2008_04
Patent number
US07365082B2

Reaction notes

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