2-Methylimidazole → 1-(4-Imidazolylsulfonyl)-2-methylimidazole

HRID 1580101Notes

Reaction equation

HRID 1580101 reaction equation
[NH:1]1[CH:5]=[C:4]([S:6](Cl)(=[O:8])=[O:7])[N:3]=[CH:2]1.[CH3:10][C:11]1[NH:12][CH:13]=[CH:14][N:15]=1>C1COCC1>[NH:1]1[CH:5]=[C:4]([S:6]([N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH3:10])(=[O:8])=[O:7])[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 127492-MethylimidazoleHCID 178527435HCID 178527435, compound

Product 1

HCID 1784329051-(4-Imidazolylsulfonyl)-2-methylimidazoleYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A dry round bottom flask equipped with a magnetic stirrer, reflux condenser and nitrogen inlet was charged with a filtered solution of 8.33 g of imidazole-4-sulfonylchloride in 300 ml of THF. The clear solution was treated with 8.45 g of 2-methylimidazole in one portion and allowed to stir overnight at room temperature. The reaction mixture was concentrated at reduced pressure to an oily residue. The residue was dissolved in 250 ml water, sodium chloride was added and the solution extracted with five 100 ml portions of ethyl acetate. The extracts were combined, washed with brine, dried (Na2SO4) and concentrated on a rotary evaporator to give 10.0 g of ivory colored product. Recrystallization from ethyl acetate-hexane have 5.57 g in two crops of 1-(4-imidazolylsulfonyl)-2-methylimidazole with mp 158°-9°, λmaxnujol 3.22 (NH), 7.30 (SO2N) and 8.48 μ (SO2N). NMR (DMSO, d6) 520-650 Hz, m, 1H; 499 Hz, d J ~ 1 Hz, 1H; 481 Hz, d, J ~ 1 Hz, 1H (AB pattern); 450 H, d, J = 1 Hz, 1H; 425 Hz, d, J = 1 Hz, 1H (AB pattern); 154 Hz, s, 3H.

Workup

  1. customA dry round bottom flask equipped with a magnetic stirrer
  2. temperaturereflux condenser and nitrogen inlet
  3. concentrationThe reaction mixture was concentrated at reduced pressure to an oily residue
  4. dissolutionThe residue was dissolved in 250 ml water
  5. additionsodium chloride was added
  6. extractionthe solution extracted with five 100 ml portions of ethyl acetate
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-e0c943498b334f0ebd29252f3ad553bf
Source dataset
uspto-grants-1976_01
Patent number
US03932444

Reaction notes

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