Hydrochloric Acid → 4,5-Dichloro-1-[2-(2,4-dichlorophenyl)hexyl]-1H-imidazole

HRID 2419340Notes

Reaction equation

HRID 2419340 reaction equation
[Na].[Cl:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[Cl:8].CS(O[CH2:14][CH:15]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27])[CH2:16][CH2:17][CH2:18][CH3:19])(=O)=O.Cl>CCOCC.O.CN(C)C=O.CO>[Cl:27][C:21]1[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=1[CH:15]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:14][N:4]1[C:3]([Cl:2])=[C:7]([Cl:8])[N:6]=[CH:5]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 1400184,5-DichloroimidazoleHCID 5360545Sodium2×HCID 19775615HCID 19775615, compound

Product 1

HCID 203061334,5-Dichloro-1-[2-(2,4-dichlorophenyl)hexyl]-1H-imidazoleYield 47%

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To 100 ml of methanol is added 1.7g (0.0735 moles) of sodium. When the sodium dissolves, 10g (0.0735 moles) of 4,5-dichlorimidazole is added. The mixture is stirred until a solution forms, and then the methanol is stripped off. The wet residue is then added to 50 ml of dimethyl formamide and the solution heated up to 125° to remove the remaining methanol and water. The solution is cooled to less than 100° and 2.5g (0.0735 moles) of 2-(2,4-dichlorophenyl)hexyl methane sulfonate is added. The reaction is heated up to 130° for 2 hours and then cooled. The reaction is poured into water and the organic material extracted three times with 200 ml of benzene. The combined extracts are washed twice with 50 ml of water, dried over anhydrous magnesium sulfate and concentrated to obtain 15.8g of the crude product. The residue is dissolved in ether, and treated with dry hydrogen chloride gas. The ether solution is decanted from the oil which forms and the oil is triturated twice with 150 ml of ether. The oil is then treated with 10% sodium hydroxide, and the product extracted out twice with 200 ml of ether. The ether solution is dried and concentrated to give 12.6g (47%) of the oil product.

Workup

  1. temperaturethe solution heated up to 125°
  2. customto remove the remaining methanol and water
  3. temperatureThe solution is cooled to less than 100°
  4. temperatureThe reaction is heated up to 130° for 2 hours
  5. temperaturecooled
  6. extractionthe organic material extracted three times with 200 ml of benzene
  7. washThe combined extracts are washed twice with 50 ml of water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customto obtain 15.8g of the crude product
  11. customThe ether solution is decanted from the oil which
  12. customthe oil is triturated twice with 150 ml of ether
  13. additionThe oil is then treated with 10% sodium hydroxide
  14. extractionthe product extracted out twice with 200 ml of ether
  15. dry with materialThe ether solution is dried
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-201ade6ca0964507b20e73a633b80fdf
Source dataset
uspto-grants-1978_08
Patent number
US04105762

Reaction notes

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