HCID 178437635, compound → HCID 178437634, compound

HRID 1580102Notes

Reaction equation

HRID 1580102 reaction equation
[NH:1]1[CH:5]=[C:4]([S:6](Cl)(=[O:8])=[O:7])[N:3]=[CH:2]1.[CH2:10]([C:12]1[NH:13][CH:14]=[C:15]([CH3:17])[N:16]=1)[CH3:11]>C1COCC1>[NH:1]1[CH:5]=[C:4]([S:6]([N:13]2[CH:14]=[C:15]([CH3:17])[N:16]=[C:12]2[CH2:10][CH3:11])(=[O:8])=[O:7])[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 178437635HCID 178437635, compoundHCID 178527435HCID 178527435, compound

Product 1

HCID 178437634HCID 178437634, compoundYield 67.5%

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 8.35 g of imidazole-4-sulfonylchloride and 180 ml of THF. The stirred solution was treated with 11.10 g of 2-ethyl-4-methylimidazole in one portion and stirred at room temperature overnight. The resulting precipitate was filtered off and the filtrate concentrated at reduced pressure to a foam. The foam was dissolved in ethyl acetate and the filtered solids partitioned between water and ethyl acetate. The combined organic layers were washed with water, dried with Na2SO4 and concentrated to give a waxy solid. Recrystallization was carried out using ethyl acetate and a small amount of hexane to give 8.13 g of 1-(4-imidazolylsulfonyl)-2-ethyl- 4-methylimidazole, mp 147°-8°, which recrystallized to mp 149°-50°, λmaxnujol 3.26 (NH), 7.30 (SO2N) and 8.68 μ (SO2N). NMR (DMSO, d6) 466 Hz, d, J = 2 Hz, 1H; 450 Hz, d, J = 2 Hz, 1H; 403 Hz, q, J = Hz, 1H; 170 Hz, q, J ~ 7.5 Hz, 2H; 116 Hz, d, J = 1 Hz, 3H; 66 Hz, t, J ~ 7.5 Hz, 3H.

Workup

  1. customA dry round bottom flask equipped with a magnetic stirrer
  2. temperaturereflux condenser and nitrogen inlet
  3. filtrationThe resulting precipitate was filtered off
  4. concentrationthe filtrate concentrated at reduced pressure to a foam
  5. dissolutionThe foam was dissolved in ethyl acetate
  6. customthe filtered solids partitioned between water and ethyl acetate
  7. washThe combined organic layers were washed with water
  8. dry with materialdried with Na2SO4
  9. concentrationconcentrated
  10. customto give a waxy solid
  11. customRecrystallization

Sources & evidence

ORD record
ord-2a2006d32fa14098b0e64694de460601
Source dataset
uspto-grants-1976_01
Patent number
US03932444

Reaction notes

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