Imidazole → HCID 178527376, compound

HRID 1580100Notes

Reaction equation

HRID 1580100 reaction equation
[NH:1]1[CH:5]=[C:4]([S:6](Cl)(=[O:8])=[O:7])[N:3]=[CH:2]1.[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1>O1CCCC1>[NH:1]1[CH:5]=[C:4]([S:6]([N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)(=[O:8])=[O:7])[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 178527435HCID 178527435, compound

Product 1

HCID 178527376HCID 178527376, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A dry round botton 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 tetrahydrofuran (THF). The clear solution was treated with 7.0 g of imidazole in one portion and allowed to stir overnight at room temperature. The reaction mixture was filtered and the filtrate concentrated to dryness. All the solids were triturated with water, filtered, rinsed with water and dried at high vacuum over NaOH. Recrystallization from ethanol gave 5.35 g of white crystals of 1-(4-imidazolylsulfonyl)imidazole mp 208°-10°, λmaxnujol 3.21 (HH), 7.29 (SO2N) and 8.52 μ (SO2N). NMR (DMSO, d6) 570-510 Hz, M, 1H; 497 Hz, t, J ~ 1 Hz, 2H; 481 Hz, d J ~ 1 Hz, 1H; 457 Hz, t, J ~ 1 Hz, 1H; 429 Hz, t, J ~ 1 Hz, 1 H.

Workup

  1. customA dry round botton flask equipped with a magnetic stirrer
  2. temperaturereflux condenser and nitrogen inlet
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate concentrated to dryness
  5. customAll the solids were triturated with water
  6. filtrationfiltered
  7. washrinsed with water
  8. dry with materialdried at high vacuum over NaOH
  9. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-1123a10a0a0442c0aabca5afd5e87bfa
Source dataset
uspto-grants-1976_01
Patent number
US03932444

Reaction notes

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