3-Chloro-1-propanol → Ternidazole

HRID 2230065Notes

Reaction equation

HRID 2230065 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1.Cl[CH2:11][CH2:12][CH2:13][OH:14]>>[OH:14][CH2:13][CH2:12][CH2:11][N:3]1[C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=[C:2]1[CH3:1]

Participants

3

Reactant 2

HCID 123133-Chloro-1-propanolHCID 127602-Methyl-5-nitroimidazole

Product 1

HCID 68944Ternidazole

Procedure

The reaction mixture of 2-methyl-5-nitroimidazole (127 g, 1.0 mol) and 1-chloro-3-hydroxypropane (500 g, 5.3 mol) will be refluxed for 24 h. Then, the excessive amount of 1-chloro-3-hydroxypropane will be removed via evaporation under a condition of 2660 Pa. To the residue, 200 ml of water will be added. The mixture will be filtered. The filtrate will be collected. The filter residue will be then rinsed with water. The water phases will be combined and alkalified with saturated sodium bicarbonate aqueous solution up to pH 9. The solution will be placed in the cold room overnight for crystallization. The crystals will be filtered, washed with water, and then dried. The crude product will be recrystallized from ethyl acetate to give 1-(3-hydroxypropyl)-2-methyl-5-nitro-1H-imidazole.

Workup

  1. temperaturewill be refluxed for 24 h
  2. customThen, the excessive amount of 1-chloro-3-hydroxypropane will be removed via evaporation under a condition of 2660 Pa
  3. additionTo the residue, 200 ml of water will be added
  4. filtrationThe mixture will be filtered
  5. customThe filtrate will be collected
  6. washThe filter residue will be then rinsed with water
  7. customThe solution will be placed in the cold room overnight for crystallization
  8. filtrationThe crystals will be filtered
  9. washwashed with water
  10. customdried
  11. customThe crude product will be recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-bad90f7f4ed643938b5ecafb5486d309
Source dataset
uspto-grants-2002_07
Patent number
US06423707B1

Reaction notes

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