Potassium Iodide → HCID 20378254, compound

HRID 2051952Notes

Reaction equation

HRID 2051952 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([S:20]([C:23]([F:28])([F:27])[CH:24]([F:26])[F:25])(=[O:22])=[O:21])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[C:35]([O:41][CH2:42]Cl)(=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37].[I-].[K+]>C(COC)OC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([S:20]([C:23]([F:28])([F:27])[CH:24]([F:25])[F:26])(=[O:21])=[O:22])[N:11]([CH2:42][O:41][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])[C:12]=2[C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 44188TiflamizoleHCID 87885Chloromethyl pivalateHCID 23665647Potassium tert-butoxide

Product 1

HCID 20378254HCID 20378254, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of 5.0 g (0.012 mole) of 4,5-bis(4-fluorophenyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole in 50 ml glyme was added 1.7 g (0.015 mole) of potassium t-butoxide, followed by a solution of 4.6 g (0.031 mole) of chloromethyl pivalate in 25 ml of glyme dropwise and a catalytic amount of potassium iodide. The reaction mixture was heated at reflux overnight, then poured onto water. The aqueous mixture was extracted with ether. The combined ether extracts were washed, then dried and concentrated to give 13.4 g of crude oily product. The product was purified by chromatography on silica gel, eluting with toluene, to give 4.1 g of crystals, mp 121°-123.5° (from methyl cyclohexane).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. additionpoured onto water
  4. extractionThe aqueous mixture was extracted with ether
  5. washThe combined ether extracts were washed
  6. customdried
  7. concentrationconcentrated
  8. customto give 13.4 g of crude oily product
  9. customThe product was purified by chromatography on silica gel
  10. washeluting with toluene

Sources & evidence

ORD record
ord-cc800ac9ec484a01bc50b9acde65b605
Source dataset
uspto-grants-1980_01
Patent number
US04182769

Reaction notes

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