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

HRID 1764305ノート

反応式

HRID 1764305 の反応式
[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

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 1400184,5-DichloroimidazoleHCID 5360545Sodium2 回HCID 19775615HCID 19775615、化合物

生成物 1

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

試薬・触媒・溶媒 4

HCID 887Methanol溶媒2 回HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

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 12.6 g (47%) of the oil product.

後処理

  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

出典と根拠

ORDレコード
ord-61e0c218ab69460aa6a6f0f6cbd6f9f4
出典データセット
uspto-grants-1978_09
特許番号
US04115578

反応ノート

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