Reaction #64225

Reaction equation

sodium hydride

product

4-(4,4-dimethyl 2,5-dioxo 3-(4-hydroxy butyl) 1-imidazolidinyl) 2-(trifluoromethyl) benzonitrile

benzyl bromide

monopotassium phosphate

→

expected product

4-(2,5-dioxo 4,4-dimethyl 3-(4-phenylmethoxy-butyl) 1-imidazolidinyl) 2-(trifluoromethyl) benzonitrile

Solvents

dimethylformamide

Conditions

Workup

1. 1
   workup.ADDITIONthe same amount of each reagent was added
2. 2
   workup.STIRRINGThe mixture was stirred for one hour
3. 3
   ExtractionExtraction
4. 4
   Washthe extracts were washed with water
5. 5
   Otherdried
6. 6
   Otherthe residue was chromatographed on silica (eluant: methylene chloride--acetone 99-1)

Procedure

48 mg of sodium hydride were added in several lots to 370 mg of the product of Example 58 in solution in 4 ml of dimethylformamide and the mixture was stirred for 30 minutes. Then, 0.12 ml of benzyl bromide and 40 mg of tetrabutylammonium iodide were added and after 90 minutes of reaction, the same amount of each reagent was added. The mixture was stirred for one hour and the reaction medium was poured into an ice-cooled aqueous solution of monopotassium phosphate. Extraction was carried out with ether and the extracts were washed with water and dried. The solvent was eliminated under reduced pressure and the residue was chromatographed on silica (eluant: methylene chloride--acetone 99-1) to obtain 140 mg of the expected product melting at 75°-76° C.

Source