Aniline → HCID 68281239, compound

HRID 1475912Notes

Reaction equation

HRID 1475912 reaction equation
[O:1]=[C:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13].CCCCCCCCCC.C(OO)(C)(C)C.NC1C=CC=CC=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.CCCCCC.C(OCC)(=O)C.O>[CH3:15][S:12]([N:11]1[C:6]2[C:5](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:4][CH:3]1[C:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:1])(=[O:14])=[O:13]

Participants

9

Reactant 4

HCID 6115AnilineHCID 6410tert-Butyl hydroperoxideHCID 15600DecaneHCID 68281255HCID 68281255, compound

Product 1

HCID 68281239HCID 68281239, compoundYield 85%

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A reactor was charged with 303 mg (1.0 mmol) of N-(2-(3-oxo-3-phenylpropyl)phenyl)methanesulfonamide (an3) obtained in Synthesis Example 7, 36.9 mg (0.10 mmol) of tetrabutylammonium iodide (Bu4N+I−), and 50 mL of ethyl acetate as a solvent to prepare a solution. Subsequently, 364 μL of 5.5 M decane solution (manufactured by Aldrich) containing 2.0 mmol of tert-butyl hydroperoxide (TBHP) as an oxidizing agent was added to the solution in an amount corresponding to 2 equivalents based on the aniline derivative (an3). After adjusting the temperature of the reaction system to room temperature (about 20° C.), the mixture was stirred for 14 hours, and then stirred (reacted) at 50° C. for 4 hours. After cooling the reaction mixture including the reaction product to room temperature, the reaction mixture was added to 20 mL of water, and extracted twice with ethyl acetate. The resulting organic layer was sequentially washed with a saturated sodium sulfite (Na2SO3) aqueous solution, an NaCl aqueous solution, and water, followed by the addition of anhydrous sodium sulfate (Na2SO4). The solvent was then evaporated under reduced pressure to obtain a concentrate including a crude product. The concentrate was subjected to silica gel flash column chromatography (eluant: hexane/ethyl acetate=6/1) to obtain (1-(methylsulfonyl)indolin-2-yl)(phenyl)methanone (white solid) represented by the following formula (as3). The yield was 85% (see Table 1-2). The analysis data for the resulting compound (as3) is shown below.

Workup

  1. customto prepare a solution
  2. additionwas added to the solution in an amount corresponding to 2 equivalents
  3. customto room temperature
  4. custom(about 20° C.)
  5. stirringstirred
  6. custom(reacted) at 50° C. for 4 hours
  7. temperatureAfter cooling the reaction mixture
  8. customto room temperature
  9. extractionextracted twice with ethyl acetate
  10. washThe resulting organic layer was sequentially washed with a saturated sodium sulfite (Na2SO3) aqueous solution
  11. additionan NaCl aqueous solution, and water, followed by the addition of anhydrous sodium sulfate (Na2SO4)
  12. customThe solvent was then evaporated under reduced pressure
  13. customto obtain a concentrate

Sources & evidence

ORD record
ord-110758459cb94afda3e216a824cd2960
Source dataset
uspto-grants-2015_04
Patent number
US09018394B2

Reaction notes

Loading…