Dimethylformamide → 1H-Imidazole, 4,5-dichloro-1-(chloromethyl)-

HRID 249356ノート

反応式

HRID 249356 の反応式
O[CH2:2][N:3]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[CH:4]1.CN(C)C=O.S(Cl)([Cl:17])=O>C(Cl)(Cl)(Cl)Cl>[Cl:17][CH2:2][N:3]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[CH:4]1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 14402691(4,5-Dichloro-1H-imidazol-1-yl)methanol

生成物 1

HCID 144026921H-Imidazole, 4,5-dichloro-1-(chloromethyl)-収率 77.1%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

94 g of 1-hydroxymethyl-4,5-dichloroimidazole is dissolved in 550 ml of carbon tetrachloride. 1 ml of dimethylformamide is added, and 100.5 g of thionyl chloride is dripped in while stirring. The mixture is refluxed until no more gas evolves, after which the solvent is removed under reduced pressure and 750 ml of methylene chloride and 250 ml of water are added to the residue. While the mixture is stirred thoroughly, its pH is brought to 7.5 with 5% strength aqueous sodium hydroxide solution. The organic phase is then separated, washed with water and dried over sodium sulfate. The residue remaining after removal of the solvent is distilled at 92° to 95° C./0.1 mbar. There is obtained 80.5 g (77%) of 1-chloromethyl-4,5-dichloroimidazole; m.p.: 40°-41° C.

後処理

  1. temperatureThe mixture is refluxed until no more gas evolves
  2. customafter which the solvent is removed under reduced pressure and 750 ml of methylene chloride and 250 ml of water
  3. additionare added to the residue
  4. stirringWhile the mixture is stirred thoroughly
  5. customThe organic phase is then separated
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customafter removal of the solvent
  9. distillationis distilled at 92° to 95° C./0.1 mbar

出典と根拠

ORDレコード
ord-0745c162f427419380a89d494e4aa805
出典データセット
uspto-grants-1993_05
特許番号
US05214064

反応ノート

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