Water → HCID 19422083, compound

HRID 273813Notes

Reaction equation

HRID 273813 reaction equation
C(=O)(O)[O-:2].[Na+].[I-].[K+].Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)=[O:15].O>CS(C)=O>[O:2]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 15388980HCID 15388980, compound

Product 1

HCID 19422083HCID 19422083, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of sodium bicarbonate (0.250 g), potassium iodide (0.050 g), and 6-bromo-N-[4-(trifluoromethyl)phenyl]hexanamide (1.00 g) in dimethylsulfoxide (15 mL) was heated at 125°-130° C. for 3.5 hours while stirring under a nitrogen atmosphere. The reaction was treated with water (75 mL) and extracted with ether. The ether extract was washed with brine (50 mL), dried over sodium sulfate after adding dichloromethane (30 mL), filtered, and concentrated in vacuo. Chromatography using 50/50 ethyl acetate/hexane gave a white solid (Rf 32 0.2 in same solvent system, 0.326 g), identified as the title compound. m.p.: 129.5°-131.0° C.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washwas washed with brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. additionafter adding dichloromethane (30 mL)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customgave a white solid (Rf 32 0.2 in same solvent system, 0.326 g)

Sources & evidence

ORD record
ord-369f3e23285d47a7948ff1739a47f7b5
Source dataset
uspto-grants-1995_02
Patent number
US05387604

Reaction notes

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