Potassium Iodide → HCID 53823829, compound

HRID 654456Notes

Reaction equation

HRID 654456 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:9][CH2:10][CH2:11]Br)=[CH:4][CH:3]=1.[CH2:20]([N:24]1[C:28](=[CH2:29])[C:27]2([CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[O:26][C:25]1=[O:35])[CH2:21][CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:9][CH2:10][CH2:11][N:32]2[CH2:33][CH2:34][C:27]3([O:26][C:25](=[O:35])[N:24]([CH2:20][CH2:21][CH2:22][CH3:23])[C:28]3=[CH2:29])[CH2:30][CH2:31]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 11187396HCID 11187396, compoundHCID 53925216HCID 53925216, compound

Product 1

HCID 53823829HCID 53823829, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10.7 g of 4,4-bis(4-chlorophenyl)-3-butenyl bromide are added to the solution of 4.5 g of 3-butyl-4-methylene-2-oxo-1-oxa-3,8-diazaspiro[4,5]decane in 45 ml of acetone containing 4.20 g of anhydrous potassium carbonate and 0.5 g of potassium iodide. The heterogeneous reaction mixture is refluxed under nitrogen while stirring for 5 hours. After evaporating the solvent under reduced pressure, water is added to the residue and extracted with benzene. The benzene phase is washed with water until halide-free, filtered through a silica gel bed and evaporated under reduced pressure. The residue is recrystallized from ethanol to give the title product in 79.0% yield, m.p.: 110°-111° C.

Workup

  1. temperatureThe heterogeneous reaction mixture is refluxed under nitrogen
  2. customAfter evaporating the solvent under reduced pressure, water
  3. additionis added to the residue
  4. extractionextracted with benzene
  5. washThe benzene phase is washed with water until halide-free
  6. filtrationfiltered through a silica gel bed
  7. customevaporated under reduced pressure
  8. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-c91390a117774a2e9e0f09c4dcaf8028
Source dataset
uspto-grants-1992_07
Patent number
US05132303

Reaction notes

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