2-Phenylimidazole → 1-(2,6-Dichlorobenzoyl)-2-phenyl-1H-imidazole

HRID 1903558Notes

Reaction equation

HRID 1903558 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:14]=1[C:15](Cl)=[O:16]>O1CCCC1>[Cl:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:14]=1[C:15]([N:11]1[CH:10]=[CH:9][N:8]=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:16]

Participants

4

Reactant 2

HCID 695912-PhenylimidazoleHCID 783922,6-Dichlorobenzoyl chloride

Product 1

HCID 30211761-(2,6-Dichlorobenzoyl)-2-phenyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

173 g of 2-phenylimidazole are dissolved in 600 ml of tetrahydrofuran. To this solution are added dropwise at boiling temperature 129.4 g of 2,6-dichlorobenzoyl chloride, dissolved in 400 ml of tetrahydrofuran, and the mixture is refluxed for 1 hour. The phenylimidazole hydrochloride which precipitates is separated at room temperature by vacuum filtration. The solvent of the filtrate is subsequently removed in the rotary evaporator, and the residue is recrystallised from 600 ml of acetonitrile. The yield after filtration with suction, washing with acetonitrile and drying is 153 g (80.4% of theory) of the product, m.p. 116°-117° C. There are obtained by concentrating the mother liquor by evaporation a further 22.3 g (11.7% of theory) of the product, m.p. 110°-114° C. For the analysis, 3.0 g of the compound are recrystallised from 5 ml of acetonitrile, washed with acetonitrile and dried at 60° C. in vacuo; yield: 2.6 g, m.p. 117°-118° C.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. customThe phenylimidazole hydrochloride which precipitates
  3. customis separated at room temperature by vacuum filtration
  4. customThe solvent of the filtrate is subsequently removed in the rotary evaporator
  5. customthe residue is recrystallised from 600 ml of acetonitrile
  6. customThe yield
  7. filtrationafter filtration with suction
  8. washwashing with acetonitrile
  9. customdrying
  10. customThere are obtained
  11. concentrationby concentrating the mother liquor
  12. customby evaporation a further 22.3 g (11.7% of theory) of the product, m.p. 110°-114° C
  13. customFor the analysis, 3.0 g of the compound are recrystallised from 5 ml of acetonitrile
  14. washwashed with acetonitrile
  15. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-d27486a046ff4a49a41fe9b9cf97dec8
Source dataset
uspto-grants-1984_03
Patent number
US04436892

Reaction notes

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