Imidazole → HCID 70606657, compound

HRID 262774Notes

Reaction equation

HRID 262774 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:12][CH2:13][CH3:14])[C:9](Cl)=[O:10].[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1.C(N(CC)CC)C.O1CCCC1>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:12][CH2:13][CH3:14])[C:9]([N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)=[O:10]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 86734157HCID 86734157, compound

Product 1

HCID 70606657HCID 70606657, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

of N-2-chlorophenyl-N-propylcarbamoyl chloride, 14g. of imidazole and 30 ml. triethylamine were refluxed in 200 ml. of dry tetrahydrofuran for five hours. The reaction mixture was poured into 2 liters of water and the slurry chilled causing some separation from the aqueous phase. A slightly sticky crystalline solid was collected, washed with water and dried in vacuo. It was recrystallised from a mixture of toluene and light petroleum (62°-68° C. fraction) with charcoaling. On cooling an oil separated which soon solidified to give the product, 1-(N-2-chlorophenyl-N-propylcarbamoyl)imidazole m.p. 75.5°-76.5° C.

Workup

  1. temperaturethe slurry chilled
  2. customsome separation from the aqueous phase
  3. customA slightly sticky crystalline solid was collected
  4. washwashed with water
  5. customdried in vacuo
  6. customIt was recrystallised from a mixture of toluene and light petroleum (62°-68° C. fraction) with charcoaling
  7. temperatureOn cooling an oil
  8. customseparated which

Sources & evidence

ORD record
ord-4806eb2739814295acff6217abf456c9
Source dataset
uspto-grants-1979_05
Patent number
US04154945

Reaction notes

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