Imidazole → HCID 70606657, compound

HRID 1730024Notes

Reaction equation

HRID 1730024 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. off imidazole and 30 ml. triethylamine were refluxed in 200 ml. of dry tetrahydrofuran for 5 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-50b103ae370d49e3b71ed8c4168a2fc2
Source dataset
uspto-grants-1976_11
Patent number
US03991071

Reaction notes

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