HCID 178418822, compound → HCID 178527377, compound

HRID 1580104Notes

Reaction equation

HRID 1580104 reaction equation
[NH:1]1[CH:5]=[C:4]([S:6](Cl)(=[O:8])=[O:7])[N:3]=[CH:2]1.[C:10]1([C:16]2[N:17]=[CH:18][NH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[NH:1]1[CH:5]=[C:4]([S:6]([N:19]2[CH:20]=[C:16]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:17]=[CH:18]2)(=[O:8])=[O:7])[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 178418822HCID 178418822, compoundHCID 178527435HCID 178527435, compound

Product 1

HCID 178527377HCID 178527377, compoundYield 87.4%

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 300 ml or THF. The solution was treated with 14.5 g of 4-phenylimidazole in one portion and the resulting solution stirred 18 hours at room temperature. The precipitate was filtered and the filtrate concentrated at reduced pressure. The solids were triturated with water, filtered, rinsed and dried at high vacuum over NaOH; then dissolved in hot ethyl acetate, treated with charcoal, filtered and concentrated to 600 ml. Hexane was added and induced crystallization. The product was filtered, rinsed and dried giving 12.02 g of white crystals in two crops of 1-(4-imidazolylsulfonyl)-4-phenylimidazole, mp 204.5-206; λmaxnujol 3.13 (NH), 7.27 (SO2N) and 8.61 μ (SO2N). NMR (DMSO, d6) 750-840 Hz, m, 1H; 495 Hz, t, J = 1Hz, 2H; 466-484 Hz, m, 4 H; 435-438 Hz, m, 3H.

Workup

  1. customA round bottom flask equipped with a magnetic stirrer
  2. temperaturereflux condenser and nitrogen inlet
  3. filtrationThe precipitate was filtered
  4. concentrationthe filtrate concentrated at reduced pressure
  5. customThe solids were triturated with water
  6. filtrationfiltered
  7. washrinsed
  8. dry with materialdried at high vacuum over NaOH
  9. dissolutionthen dissolved in hot ethyl acetate
  10. additiontreated with charcoal
  11. filtrationfiltered
  12. concentrationconcentrated to 600 ml
  13. additionHexane was added
  14. customcrystallization
  15. filtrationThe product was filtered
  16. washrinsed
  17. customdried

Sources & evidence

ORD record
ord-408386810e984a92a3f672e4f952b5c3
Source dataset
uspto-grants-1976_01
Patent number
US03932444

Reaction notes

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