1H-Imidazole, 2-(1-methylethyl)- → 1-(4-Imidazolylsulfonyl)-2-isopropylimidazole

HRID 1580105Notes

Reaction equation

HRID 1580105 reaction equation
[NH:1]1[CH:5]=[C:4]([S:6](Cl)(=[O:8])=[O:7])[N:3]=[CH:2]1.[CH:10]([C:13]1[NH:14][CH:15]=[CH:16][N:17]=1)([CH3:12])[CH3:11]>C1COCC1>[NH:1]1[CH:5]=[C:4]([S:6]([N:14]2[CH:15]=[CH:16][N:17]=[C:13]2[CH:10]([CH3:12])[CH3:11])(=[O:8])=[O:7])[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 1234571H-Imidazole, 2-(1-methylethyl)-HCID 178527435HCID 178527435, compound

Product 1

HCID 1784401171-(4-Imidazolylsulfonyl)-2-isopropylimidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A round bottom flask equipped with a magnetic stirrer, reflux condenser and nitrogen inlet was charged with 8.35 g of imidazole-4-sulfonylchloride and 150 ml of THF. This solution was treated with 11.10 g of 2-isopropylimidazole in one portion and the solution stirred 24 hours at room temperature. The solution was concentrated to a clear oil and partitioned between ethylacetate and water. The organic layer was washed with water and the water washes back extracted with ethyl acetate. The organic layer was dried (Na2SO4) and concentrated to a foam. The foam was dissolved in acetone and chromatographed on activity III alumina to separate 1-(4-imidazolylsulfonyl)-2-isopropylimidazole, mp 118°-120°.

Workup

  1. customA round bottom flask equipped with a magnetic stirrer
  2. temperaturereflux condenser and nitrogen inlet
  3. concentrationThe solution was concentrated to a clear oil
  4. custompartitioned between ethylacetate and water
  5. washThe organic layer was washed with water
  6. extractionthe water washes back extracted with ethyl acetate
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. concentrationconcentrated to a foam
  9. dissolutionThe foam was dissolved in acetone
  10. customchromatographed on activity III alumina
  11. customto separate 1-(4-imidazolylsulfonyl)-2-isopropylimidazole, mp 118°-120°

Sources & evidence

ORD record
ord-b6530124932e4f42a00c3876472dab12
Source dataset
uspto-grants-1976_01
Patent number
US03932444

Reaction notes

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