Water → HCID 19422083, compound

HRID 744691Notes

Reaction equation

HRID 744691 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 =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 Chromatography
  8. customgave a white solid (Rf =0.2 in same solvent system, 0.326 g)

Sources & evidence

ORD record
ord-6e3b422bbdcb4e53a08f404ad31aeea6
Source dataset
uspto-grants-1996_09
Patent number
US05559143

Reaction notes

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