Potassium Carbonate → HCID 18437793, compound

Temperature

0 °C

1-Butyl-5-hydroxymethyl-2-iodo-4-phenylimidazole (1.96 g, 6.1 mmol) is dissolved in 20 ml dichloromethane and cooled to 0° C. To the solution is added 5 equivalents of thionyl chloride and the resulting solution is stirred at room temperature for 2 h. The reaction mixture is evaporated at reduced pressure and 20 ml of toluene is added to the residue and evaporated to remove any residual thionyl chloride. The crude product is dissolved in 20 ml of anhydrous acetonitrile and added to an ice-cooled solution of piperonyl amine (2.0 eq.) in acetonitrile (10 mL) containing potassium carbonate (2 eq.). The resulting mixture is stirred at room temperature for 4 h, diluted with 100 ml of ethyl acetate, washed with water and brine, dried over sodium sulfate and concentrated at reduced pressure. The residue is purified by silica gel chromatography (hexanes/ethyl acetate, from 2:1 to 1:1) to give 2.28 g of 1-butyl-5-chloromethyl-2-iodo-4-phenylimidazole. MS (+VE) m/z 490 (M+1).

1. customThe reaction mixture is evaporated at reduced pressure and 20 ml of toluene
2. additionis added to the residue
3. customevaporated
4. customto remove any residual thionyl chloride
5. dissolutionThe crude product is dissolved in 20 ml of anhydrous acetonitrile
6. additionadded to an ice-
7. stirringThe resulting mixture is stirred at room temperature for 4 h
8. washwashed with water and brine
9. dry with materialdried over sodium sulfate
10. concentrationconcentrated at reduced pressure
11. customThe residue is purified by silica gel chromatography (hexanes/ethyl acetate, from 2:1 to 1:1)

ORD record

ord-48802fb7044f4006bcbf692b61b2bd0a

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119665B2