4,5-Dimethyl-1H-imidazole → 2,3-Dimethyl-8-(2,4-dichlorophenyl)-5,6-dihydroimidazo[1,2-a]pyridine

HRID 488728Notes

Reaction equation

HRID 488728 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH:11]1[CH2:13][CH2:12]1)=O.[CH3:14][C:15]1[N:16]=[CH:17][NH:18][C:19]=1[CH3:20]>C(OCC)(=O)C>[CH3:14][C:15]1[N:16]=[C:17]2[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[CH:11][CH2:13][CH2:12][N:18]2[C:19]=1[CH3:20]

Participants

4

Reactant 2

HCID 753064,5-Dimethyl-1H-imidazoleHCID 22267309Cyclopropyl 2,4-dichlorophenyl ketone

Product 1

HCID 222673202,3-Dimethyl-8-(2,4-dichlorophenyl)-5,6-dihydroimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
205 °C

Procedure

Cyclopropyl 2,4-dichlorophenyl ketone (1) (54 g, 0.25 mol) and 4,5-dimethylimidazole (2) (90 g, 1 mol) are combined and heated at 200 to 210° C. under nitrogen for 20 hours. The reaction is cooled and diluted with ethyl acetate (700 ml). The ethyl acetate solution is washed with saturated aq potassium carbonate (300 ml) and water (4×200 ml) and dried over sodium sulfate. The drying agent is removed by filtration and the solvent is removed in vacuo to provide 3.

Workup

  1. temperatureThe reaction is cooled
  2. washThe ethyl acetate solution is washed with saturated aq potassium carbonate (300 ml) and water (4×200 ml)
  3. dry with materialdried over sodium sulfate
  4. customThe drying agent is removed by filtration
  5. customthe solvent is removed in vacuo
  6. customto provide 3

Sources & evidence

ORD record
ord-f1ad79397d9f4ac497432fa1879003e8
Source dataset
uspto-grants-2005_12
Patent number
US06974808B2

Reaction notes

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