Reaction #55723

Reaction equation

water

sodium

imidazole

1-(2',4'-dichlorophenyl)-2-chloro-ethanol

→

desired product

Yield 66.3%

1-(2',4'-dichlorophenyl)-2-(N-imidazolyl)-ethanol

Yield 66.3%

Solvents

methanol

dimethylformamide

Conditions

Workup

1. 1
   Otherthe solvent was then evaporated off
2. 2
   workup.DISSOLUTIONThe residue was dissolved in 300 ml of dimethylformamide
3. 3
   Temperatureheated to 115°-120° C
4. 4
   OtherTo the solution so obtained
5. 5
   workup.ADDITIONwas added
6. 6
   TemperatureThe mixture was heated to 115°-120° C.
7. 7
   Temperaturemaintained at that temperature for 20 minutes
8. 8
   OtherThe product precipitated
9. 9
   workup.STIRRINGunder stirring over a period of about two hours
10. 10
    Otherthe upper liquid was then decanted off
11. 11
    workup.ADDITIONa further 2500 ml of water were added
12. 12
    Filtrationthe whole was filtered
13. 13
    OtherThe precipitate thus obtained
14. 14
    Otherwas dried
15. 15
    Othercrystallized from toluene

Procedure

30 g of sodium were added to a solution of 88.5 g of imidazole in 600 ml of methanol; the solvent was then evaporated off. The residue was dissolved in 300 ml of dimethylformamide and heated to 115°-120° C. To the solution so obtained was added, dropwise and under stirring, a solution of 225 g of 1-(2',4'-dichlorophenyl)-2-chloro-ethanol in 400 ml of dimethylformamide. The mixture was heated to 115°-120° C. and maintained at that temperature for 20 minutes and, after subsequent cooling to 40° C., 2500 ml of iced water were added under vigorous stirring. The product precipitated under stirring over a period of about two hours, the upper liquid was then decanted off, a further 2500 ml of water were added and, after standing, the whole was filtered. The precipitate thus obtained was dried and crystallized from toluene. 170 g of the desired product, melting at 134°-135° C., was obtained.

Source