Potassium Iodide → HCID 19814359, compound

HRID 466618Notes

Reaction equation

HRID 466618 reaction equation
[CH2:1]([N:5]1[C:9]([OH:11])([CH3:10])[C:8]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[O:7][C:6]1=[O:17])[CH2:2][CH2:3][CH3:4].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[CH:26][CH2:27][CH2:28]Br)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(C(C)=O)C(C)C.CCOCC>[ClH:18].[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]([C:30]2[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=2)=[CH:26][CH2:27][CH2:28][N:14]2[CH2:13][CH2:12][C:8]3([O:7][C:6](=[O:17])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:9]3([OH:11])[CH3:10])[CH2:16][CH2:15]2)=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 11187396HCID 11187396, compoundHCID 19814230HCID 19814230, compound

Product 1

HCID 19814359HCID 19814359, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture containing 7.27 g of 3-butyl-4-hydroxy-4-methyl-2-oxo-1-oxa-3,8-diazaspiro[4,5]decane, 12.89 g of 4,4-bis(4-chlorophenyl)-3-butenyl bromide, 4.98 g of anhydrous potassium carbonate and 0.6 g of potassium iodide in 73 ml of methyl isobutyl ketone is gently refluxed under argon while stirring for 6 hours. After cooling down, the inorganic salts are filtered off, washed with methyl isobutyl ketone, the filtrate is washed with water to neutral, dried over anhydrous magnesium sulfate and then the solvent is distilled off under reduced pressure. After recrystallizing the evaporation residue from ethanol, the product obtained is dissolved in ether and the hydrochloride is precipitated by adding ethereal hydrogen chloride solution to obtain 79.3% of the title hydrochloride, m.p.: 230°-233° C. (with decomposition).

Workup

  1. temperatureis gently refluxed under argon
  2. temperatureAfter cooling down
  3. filtrationthe inorganic salts are filtered off
  4. washwashed with methyl isobutyl ketone
  5. washthe filtrate is washed with water to neutral,
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off under reduced pressure
  8. customAfter recrystallizing the evaporation residue from ethanol
  9. customthe product obtained
  10. customthe hydrochloride is precipitated
  11. additionby adding ethereal hydrogen chloride solution

Sources & evidence

ORD record
ord-afb1622deac741dc89e02a0bd0575f0b
Source dataset
uspto-grants-1992_10
Patent number
US05157038

Reaction notes

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