2-Chloro-N,N-dimethylethylamine → 2-(2-Dimethylaminoethylthio)-1-(3,5-difluorobenzyl)imidazole dihydrochloride

HRID 1165935ノート

反応式

HRID 1165935 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([F:15])[CH:14]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[SH:11].[OH-].[K+].[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21][Cl:22].Cl.CN(CC[Cl:30])C.[OH-].[Na+]>CN(C)C=O.C1(C)C=CC=CC=1.O>[ClH:22].[ClH:30].[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21][S:11][C:7]1[N:6]([CH2:5][C:4]2[CH:3]=[C:2]([F:1])[CH:14]=[C:13]([F:15])[CH:12]=2)[CH:10]=[CH:9][N:8]=1

参加物

10

反応物 5

HCID 79012-Chloro-N,N-dimethylethylamineHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 178505924HCID 178505924、化合物

生成物 1

HCID 198613862-(2-Dimethylaminoethylthio)-1-(3,5-difluorobenzyl)imidazole dihydrochloride

試薬・触媒・溶媒 4

HCID 962Water触媒HCID 962Water溶媒HCID 1140Toluene溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

1-(3,5-Difluorobenzyl)-2-mercaptoimidazole (2.26 g, 0.010) and potassium hydroxide (0.056 g, 0.010 mole) are dissolved in dimethylformamide (10 ml) containing water (0.5 ml) with stirring under argon at ambient temperature. To this solution is added dropwise 2-dimethylaminoethyl chloride (1.08 g, 0.010 mole) in toluene (10 ml). [This solution is prepared by stirring 1.44 g of dimethylaminoethyl chloride hydrochloride with an excess of sodium hydroxide pellets in the presence of toluene (10 ml) and a few drops of water, followed by filtering the solution of neutralized base.] The reaction mixture is warmed to 95° C., stirred at this temperature for one hour, cooled and then diluted with water. The layers are shaken together and separated and then the aqueous phase is extracted twice with ether. The toluene and ether extracts are combined and the solvents are removed in vacuo. The residual oil is dissolved in ether and hydrogen chloride in ether is added slowly with stirring until a slight excess is present. The precipitated white crystalline solid is filtered and recrystallized from ethanol ether to give 2-(2-dimethylaminoethylthio)-1-(3,5-difluorobenzyl)imidazole dihydrochloride.

後処理

  1. custom[This solution is prepared
  2. filtrationby filtering the solution of neutralized base
  3. temperature] The reaction mixture is warmed to 95° C.
  4. stirringstirred at this temperature for one hour
  5. temperaturecooled
  6. additiondiluted with water
  7. stirringThe layers are shaken together
  8. customseparated
  9. extractionthe aqueous phase is extracted twice with ether
  10. customthe solvents are removed in vacuo
  11. dissolutionThe residual oil is dissolved in ether
  12. additionhydrogen chloride in ether is added slowly
  13. stirringwith stirring until a slight
  14. filtrationThe precipitated white crystalline solid is filtered
  15. customrecrystallized from ethanol ether

出典と根拠

ORDレコード
ord-bb9cf55264544175a7b64486879b4fcd
出典データセット
uspto-grants-1990_03
特許番号
US04912226

反応ノート

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