Reacción #6577

Ecuación de reacción

NCS

2-n-butyl-1-(2-chlorophenyl)methyl-5-hydroxymethyl-1H-imidazole

N-chlorosuccinimide

→

2-n-butyl 4-chloro 1-(2-chlorophenyl)methyl-5-hydroxymethyl-1H-imidazole

Rendimiento 44.2%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe tetrahydrofuran was evaporated
2. 2
   Otrothe residue was partitioned between water and ethyl acetate
3. 3
   LavadoThe organic extracts were washed with water
4. 4
   Otrodried
5. 5
   Concentraciónconcentrated to the residual product
6. 6
   Otrothat crystallized when
7. 7
   workup.STIRRINGstirred with ether

Procedimiento

A solution of 2-n-butyl-1-(2-chlorophenyl)methyl-5-hydroxymethyl-1H-imidazole (Example 3(i) Method A) (10.2 g. 0.0368 mol) in tetrahydrofuran (100 ml) was treated portionwise with N-chlorosuccinimide (NCS) (4.92 g, 0.0368 mol) and stirred at 45° C. for a total of 3 hours after the addition of the NCS. The tetrahydrofuran was evaporated and the residue was partitioned between water and ethyl acetate. The organic extracts were washed with water, dried and concentrated to the residual product that crystallized when stirred with ether to yield 5.1 g (44%) of 2-n-butyl 4-chloro 1-(2-chlorophenyl)methyl-5-hydroxymethyl-1H-imidazole; mp 134°-135° C. (from acetonitrile).

Fuente