Reaction #66480

Reaction equation

(RS)-1-(cyclopropylsulfinyl)-4-nitrobenzene

potassium carbonate

iodobenzene diacetate

magnesium oxide

trifluoroacetamide

→

(RS)—S-(4-nitrophenyl)-S-cyclopropylsulfoximide

Solvents

dichloro-methane

methanol

water

Conditions

Workup

1. 1
   workup.STIRRINGstirred at room temperature for 12 hours
2. 2
   workup.STIRRINGstirred at room temperature for 4 hours
3. 3
   Otherthe organic phase is separated
4. 4
   Filtrationfiltered at the pump through Celite®
5. 5
   ExtractionThe aqueous phase is extracted several times with dichloromethane
6. 6
   WashThe combined organic phases are washed with half-saturated sodium chloride solution
7. 7
   workup.STIRRINGstirred with 100 ml 2N hydrochloric acid for 30 minutes
8. 8
   Washwashed with water
9. 9
   Otherdried
10. 10
    Other4.7 g (66.5% of theor.) of the product is obtained

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.

Source