Imidazole → HCID 20291998, compound

HRID 1730029Notes

Reaction equation

HRID 1730029 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[O:6]([CH2:13][CH2:14][N:15]([CH2:19][CH2:20][CH3:21])[C:16](Cl)=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O1CCCC1>[O:6]([CH2:13][CH2:14][N:15]([CH2:19][CH2:20][CH3:21])[C:16]([N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 12238093Carbamic chloride, (2-phenoxyethyl)propyl-

Product 1

HCID 20291998HCID 20291998, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 75 ml. dry tetrahydrofuran were added 6.8 g. imidazole and 12.075 g. N-2-phenoxyethyl-N-propylcarbamoyl chloride. The reactants were boiled together under reflux for 24 hours, cooled to room temperature and filtered to remove imidazole hydrochloride. The solvent was then removed by evaporation from the steam bath, the last traces being removed under vacuum. An oily residue remained which was extracted into ether, washed with water, dried over anhydrous sodium sulphate, the solvent removed and the residual oil distilled under vacuum, to give 1-(N-2-phenoxyethyl-N-propylcarbamoyl) imidazole, boiling point 209° C./1.0 mm.

Workup

  1. temperatureunder reflux for 24 hours
  2. filtrationfiltered
  3. customto remove imidazole hydrochloride
  4. customThe solvent was then removed by evaporation from the steam bath
  5. customthe last traces being removed under vacuum
  6. extractionwas extracted into ether
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulphate
  9. customthe solvent removed
  10. distillationthe residual oil distilled under vacuum

Sources & evidence

ORD record
ord-bf3250be4d054e14bb73357c4c8eddb0
Source dataset
uspto-grants-1976_11
Patent number
US03991071

Reaction notes

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