Imidazole → HCID 19377695, compound

HRID 2210802Notes

Reaction equation

HRID 2210802 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][CH2:8]CS([O-])(=O)=O.[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][CH2:8][N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 19377732HCID 19377732, compound

Product 1

HCID 19377695HCID 19377695, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 17.8 g of [2-(1-methyl-1H-pyrrol-2-yl)ethyl]methanesulfonate (ester), 11.7 g of 1H-imidazole, 14 g of potassium carbonate and 410 ml of tetrahydrofuran was stirred for 3 days at reflux temperature. After cooling, the reaction mixture was evaporated and the residue was taken up in water. The product was extracted with dichloromethane and the extract was dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2C12 /CH3OH 95:5). The eluent of the desired fraction was evaporated and the residue was co-evaporated with methylbenzene (3×). The product was filtered off and dried, yielding 9.3 g (61.7%) of 1-[2-(1-methyl-1H-pyrrol-2-yl)ethyl]-1H-imidazole (interm. 1);

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated
  4. extractionThe product was extracted with dichloromethane
  5. customthe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography (silica gel
  9. customThe eluent of the desired fraction was evaporated
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-c254b88c9996488099aa8028a8a979b7
Source dataset
uspto-grants-1995_10
Patent number
US05461050

Reaction notes

Loading…