Potassium Iodide → HCID 22508626, compound

HRID 458619

Reaction equation

HRID 458619 reaction equation
[Cl:1][C:2]1[NH:11][C:10]2[C:9](=[O:12])[N:7]([CH3:8])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=1.[I:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C.CCOC(C)=O.O>[Cl:1][C:2]1[N:11]([CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[I:15])[C:10]2[C:9](=[O:12])[N:7]([CH3:8])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 106618-ChlorotheophyllineHCID 11430Potassium CarbonateHCID 1010641-(Chloromethyl)-2-iodobenzene

Product 1

HCID 22508626HCID 22508626, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

8-Chlorotheophylline (8.5 g, 39.6 mmol) was dissolved in 400 ml of DMF and 2-iodobenzyl chloride (10.0 g, 39.6 mmol), potassium carbonate (5.47 g, 39.6 mmol), and potassium iodide (10 mg, 0.06 mmol) were added. The mixture was stirred at room temperature for 7 days. Water (2500 ml) and EtOAc (800 ml) were added and the layers were separated. The aqueous layer was extracted with 2×500 ml of EtOAc, and the combined organic layer was washed with 500 ml of water, 500 ml of brine, dried over sodium sulphate, and filtered. The solvent was evaporated and the crude product was crystallized from diethyl ether and petrol, to give compound (5A) as white crystals. The mother liquor was evaporated and resuspended in diethyl ether and petrol, to give a second crop of compound (5A).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with 2×500 ml of EtOAc
  3. washthe combined organic layer was washed with 500 ml of water, 500 ml of brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customThe solvent was evaporated
  7. customthe crude product was crystallized from diethyl ether and petrol

Sources & evidence

ORD record
ord-7334a02c700b42bdb9c1f534b68ac804
Source dataset
uspto-grants-2007_03
Patent number
US07192952B2

Linked notes

Loading…