2-Propylimidazole → HCID 178440118, compound

HRID 1580103Notes

Reaction equation

HRID 1580103 reaction equation
[NH:1]1[CH:5]=[C:4]([S:6](Cl)(=[O:8])=[O:7])[N:3]=[CH:2]1.[CH2:10]([C:13]1[NH:14][CH:15]=[CH:16][N:17]=1)[CH2:11][CH3:12]>C1COCC1>[NH:1]1[CH:5]=[C:4]([S:6]([N:14]2[CH:15]=[CH:16][N:17]=[C:13]2[CH2:10][CH2:11][CH3:12])(=[O:8])=[O:7])[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 1626172-PropylimidazoleHCID 178527435HCID 178527435, compound

Product 1

HCID 178440118HCID 178440118, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A round bottom flask equipped with a magnetic stirrer, reflux condenser and nitrogen inlet was charged with 10.85 g of imidazole-4-sulfonylchloride and 180 ml of THF. This solution was treated with a solution of 15.4 g 2-n-propylimidazole in 100 ml of THF. The reaction mixture was stirred at room temperature overnight and then refluxed 48 hours. The clear solution was concentrated to an oil and dissolved in water. The opaque solution deposited crystals on standing which were filtered, washed and dried. Recrystallization from ethyl acetate gave 10.61 g of white crystals of 1-(4-imidazolylsulfonyl)-2-n-propylimidazole with mp 163°-4°, λmaxnujol 3.18 (NH), 7.32 (SO2N) and 8.52 μ (SO2N). NMR (DMSO, d6): 660-730 Hz, m, 1H; 496 Hz, d, J = 1.5 Hz, 1H; 477 Hz, d, J = 1.5 Hz, 1H; 447 Hz, d, J = 2 Hz, 1H; 415 Hz, d, J = 2 Hz, 1H; 174 Hz, t, J = 7 Hz, 2H; 82-118 Hz, sextet, J = 7 Hz, 2H; 51 Hz, t, J = 7 Hz, 3H.

Workup

  1. customA round bottom flask equipped with a magnetic stirrer
  2. temperaturereflux condenser and nitrogen inlet
  3. temperaturerefluxed 48 hours
  4. concentrationThe clear solution was concentrated to an oil
  5. dissolutiondissolved in water
  6. filtrationwere filtered
  7. washwashed
  8. customdried
  9. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-acc65de74c7a4b5bb8fabc6b4ab7706f
Source dataset
uspto-grants-1976_01
Patent number
US03932444

Reaction notes

Loading…