Reaktion #6577

Reaktionsgleichung

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

Ausbeute 44.2%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe tetrahydrofuran was evaporated
2. 2
   Sonstigethe residue was partitioned between water and ethyl acetate
3. 3
   WaschenThe organic extracts were washed with water
4. 4
   Sonstigedried
5. 5
   Einengenconcentrated to the residual product
6. 6
   Sonstigethat crystallized when
7. 7
   workup.STIRRINGstirred with ether

Vorschrift

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).

Quelle