Thiophenol → HCID 69002841, compound

HRID 1951608Notes

Reaction equation

HRID 1951608 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)[S:7][C:8]=1[CH2:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH3:32])S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)=[CH:15][CH:14]=1)=[O:12])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1>CN(C)C=O.O>[CH:1]([C:4]1[N:5]=[C:6]([C:33]2[CH:34]=[CH:35][C:36]([C:39]([F:41])([F:42])[F:40])=[CH:37][CH:38]=2)[S:7][C:8]=1[CH2:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([NH:19][CH3:32])=[CH:15][CH:14]=1)=[O:12])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 69000159HCID 69000159, compound

Product 1

HCID 69002841HCID 69002841, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The obtained N-[4-[3-[4-isopropyl-2-[4-(trifluoromethyl)phenyl]thiazol-5-yl]propionyl]phenyl]-N-methyl-2-nitrobenzenesulfonamide (230 mg, 0.372 mmol) was dissolved in anhydrous dimethylformamide (5 mL). Potassium carbonate (154 mg, 1.116 mmol) and thiophenol (46 μL, 0.446 mmol) were added to the solution. The mixture was stirred at room temperature for 1 hour. The mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous sodium bicarbonate solution, and saturated brine, and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography with hexane/ethyl acetate (8:2, v/v) to give the desired compound (154 mg) as yellow crystalline product (yield 95%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium bicarbonate solution, and saturated brine, and dried with anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography with hexane/ethyl acetate (8:2, v/v)

Sources & evidence

ORD record
ord-e39e39e494f644fab551a572448d1dcd
Source dataset
uspto-grants-2013_03
Patent number
US08404726B2

Reaction notes

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