Potassium Iodide → HCID 19737404, compound

HRID 258338Notes

Reaction equation

HRID 258338 reaction equation
[Na].[NH:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[Cl:7][C:8]1[CH:9]=[C:10]([CH:27]=[CH:28][CH:29]=1)[O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2([CH2:25]Br)[O:22][CH:21]([CH2:23][CH3:24])[CH2:20][O:19]2)=[CH:14][CH:13]=1.[I-].[K+]>CN(C)C=O.O>[Cl:7][C:8]1[CH:9]=[C:10]([CH:27]=[CH:28][CH:29]=1)[O:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2([CH2:25][C:3]3[NH:2][CH:6]=[CH:5][N:4]=3)[O:22][CH:21]([CH2:23][CH3:24])[CH2:20][O:19]2)=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 197374082-(Bromomethyl)-2-[4-(3-chlorophenoxy)phenyl]-4-ethyl-1,3-dioxolaneHCID 57373095Imidazole sodium

Product 1

HCID 19737404HCID 19737404, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.2 parts of imidazole sodium salt, 4 parts of 2-[p-(3chlorophenoxy)phenyl]-2-bromomethyl-4-ethyl-1,3-dioxolane and a catalytic amount of potassium iodide are stirred in 50 ml of dimethyl formamide for 17 hours at a temperature of 125° C. The brown reaction mixture is cooled to room temperature, diluted with 150 ml of water and extracted with three 50 ml portions of ethyl acetate. The combined extracts are washed with two 50 ml portions of water, and dried over sodium sulfate. The solvent is removed by evaporation and the crude product is chromatographed over a 35 cm column of silica gel with acetone/ethyl acetate (1:1). The eluant is removed by evaporation and the oily residue is crystallised from petroleum ether in the form of slightly yellowish crystals with a melting point of 69°-71° C.

Workup

  1. extractionextracted with three 50 ml portions of ethyl acetate
  2. washThe combined extracts are washed with two 50 ml portions of water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is removed by evaporation
  5. customthe crude product is chromatographed over a 35 cm column of silica gel with acetone/ethyl acetate (1:1)
  6. customThe eluant is removed by evaporation
  7. customthe oily residue is crystallised from petroleum ether in the form of slightly yellowish crystals with a melting point of 69°-71° C.

Sources & evidence

ORD record
ord-e15590ecf20b4100862e6e6906885d60
Source dataset
uspto-grants-1993_11
Patent number
US05266585

Reaction notes

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