Potassium Carbonate → 1-(Cyclopropanesulfonimidoyl)-4-nitrobenzene

HRID 238133

Reaction equation

HRID 238133 reaction equation
[CH:1]1([S:4]([C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)=[O:5])[CH2:3][CH2:2]1.FC(F)(F)C([NH2:19])=O.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.[O-2].[Mg+2].C(=O)([O-])[O-].[K+].[K+]>ClCCl.CO.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2].O>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([S:4]([CH:1]2[CH2:3][CH2:2]2)(=[NH:19])=[O:5])=[CH:7][CH:8]=1)([O-:14])=[O:13]

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 67717TrifluoroacetamideHCID 6850729Magnesium monoxideHCID 12217721Iodo benzene diacetateHCID 595508341-(Cyclopropanesulfinyl)-4-nitrobenzene

Product 1

HCID 569492531-(Cyclopropanesulfonimidoyl)-4-nitrobenzene

Reagents, catalysts & solvents 4

HCID 152122Dirhodium tetraacetateCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

6.6 g (31.24 mmol) (RS)-1-(cyclopropylsulfinyl)-4-nitrobenzene, 7.77 g trifluoroacetamide (68.74 mmol), 16.6 g (51.55 mmol) iodobenzene diacetate and 5.54 g (137.5 mmol) magnesium oxide are placed in 350 ml dichloro-methane. The mixture is stirred for 5 minutes, treated with 0.69 g (1.56 mmol) rhodium(II) acetate dimer and stirred at room temperature for 12 hours. The suspension is diluted with 235 ml methanol, treated with 23.75 g potassium carbonate and stirred at room temperature for 4 hours. Next the mixture is treated with 400 ml water, and the organic phase is separated and filtered at the pump through Celite®. The aqueous phase is extracted several times with dichloromethane. The combined organic phases are washed with half-saturated sodium chloride solution and stirred with 100 ml 2N hydrochloric acid for 30 minutes. The aqueous phase is adjusted to pH 9 with concentrated sodium hydroxide solution with ice cooling. The crystallised product is aspirated dry, washed with water and dried. 4.7 g (66.5% of theor.) of the product is obtained.

Workup

  1. stirringstirred at room temperature for 12 hours
  2. stirringstirred at room temperature for 4 hours
  3. customthe organic phase is separated
  4. filtrationfiltered at the pump through Celite®
  5. extractionThe aqueous phase is extracted several times with dichloromethane
  6. washThe combined organic phases are washed with half-saturated sodium chloride solution
  7. stirringstirred with 100 ml 2N hydrochloric acid for 30 minutes
  8. washwashed with water
  9. customdried
  10. custom4.7 g (66.5% of theor.) of the product is obtained

Sources & evidence

ORD record
ord-316d629c237c41b6b05d4e126ba5b725
Source dataset
uspto-grants-2014_02
Patent number
US08642611B2

Linked notes

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