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

HRID 1198153Notes

Reaction equation

HRID 1198153 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6ed8f606396d4991be24279c10d5c850
Source dataset
uspto-grants-1994_01
Patent number
US05280036

Reaction notes

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