Réaction #6577

Équation de réaction

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

Rendement 44.2%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   AutreThe tetrahydrofuran was evaporated
2. 2
   Autrethe residue was partitioned between water and ethyl acetate
3. 3
   LavageThe organic extracts were washed with water
4. 4
   Autredried
5. 5
   Concentrationconcentrated to the residual product
6. 6
   Autrethat crystallized when
7. 7
   workup.STIRRINGstirred with ether

Mode opératoire

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).

Source