Imidazole → HCID 70606657, compound

HRID 1679386Notes

Reaction equation

HRID 1679386 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
  8. customan oil separated which

Sources & evidence

ORD record
ord-27d7552a05584af4a1911264e6776dab
Source dataset
uspto-grants-1978_03
Patent number
US04080462

Reaction notes

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