Potassium Iodide → HCID 15572233, compound

HRID 2286598Notes

Reaction equation

HRID 2286598 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([C:9]([OH:18])([C:14]([F:17])([F:16])[Cl:15])[C:10]([F:13])([F:12])[Cl:11])[CH:6]=[C:5]([CH3:19])[C:3]=1[NH2:4].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].[I-].[K+].C([O-])(O)=O.[Na+]>CC#N>[CH2:25]([O:24][C:22]([CH2:21][NH:4][C:3]1[C:2]([CH3:1])=[CH:8][C:7]([C:9]([OH:18])([C:10]([F:12])([F:13])[Cl:11])[C:14]([F:16])([F:17])[Cl:15])=[CH:6][C:5]=1[CH3:19])=[O:23])[CH3:26]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 516892Sodium BicarbonateHCID 15572232HCID 15572232, compound

Product 1

HCID 15572233HCID 15572233, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Combine 2,6-dimethyl-4-(tetrafluoro-1,3-dichloro-2-hydroxy-2-propyl)aniline [Gilbert, et. al., J. Org. Chem., 30, 1001 (1965)] (26 g=0.08 mol) with ethyl bromoacetate (22 g=0.13 mol) and potassium iodide (22 g=0.13 mol) in 150 ml CH3CN. Heat to reflux and add NaHCO3 (13.4 g=0.16 mol). Heat at reflux 20 hours, allow to cool, pour onto water, and extract with Et2O. Wash the Et2O with 10% Na2CO3, then 1 N HCl. Dry over MgSO4 and filter. Add 4 N HCl/Et2O and dilute with an equal volume of hexane. Decant and wash the solid with benzene. Partition the solid between 10% Na2CO3 and Et2O. Dry and concentrate the Et2O. Recrystallize the residue from hexane to obtain the title product as a white solid, melting at about 102°-104° C.

Workup

  1. temperatureHeat
  2. temperatureto reflux
  3. temperatureHeat
  4. temperatureat reflux 20 hours
  5. temperatureto cool
  6. additionpour onto water
  7. extractionextract with Et2O
  8. washWash the Et2O with 10% Na2CO3
  9. dry with materialDry over MgSO4
  10. filtrationfilter
  11. additionAdd 4 N HCl/Et2O
  12. additiondilute with an equal volume of hexane
  13. customDecant
  14. washwash the solid with benzene
  15. customPartition the solid between 10% Na2CO3 and Et2O
  16. customDry
  17. concentrationconcentrate the Et2O
  18. customRecrystallize the residue from hexane

Sources & evidence

ORD record
ord-9202ece23af04de590118c29b47589f6
Source dataset
uspto-grants-1981_05
Patent number
US04267193

Reaction notes

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