Sulfuric Acid → S-Methyl-S-(4-nitrophenyl)sulfoximine

HRID 38199

Reaction equation

HRID 38199 reaction equation
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)=[O:3].[N-:13]=[N+]=[N-].[Na+].S(=O)(=O)(O)O>C(Cl)(Cl)Cl>[N+:10]([C:7]1[CH:6]=[CH:5][C:4]([S:2]([CH3:1])(=[NH:13])=[O:3])=[CH:9][CH:8]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 3058821-(Methylsulfinyl)-4-nitrobenzene

Product 1

HCID 12463933S-Methyl-S-(4-nitrophenyl)sulfoximine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
45 °C

Procedure

23.65 g (127.7 mmol) (RS)-1-(methylsulfinyl)-4-nitrobenzene in 130 ml chloroform are treated with 9.32 g (143.4 mmol) sodium azide. The mixture is slowly treated with 32.4 ml of concentrated sulfuric acid at 0° C. and then slowly heated to 45° C. After 16 hrs, the mixture is cooled to room temperature, treated with ice-water and extracted with chloroform. This organic phase is discarded. The aqueous phase is basified with 2N NaOH solution and extracted with DCM. The combined organic phases are washed with saturated NaCl solution, dried (Na2SO4), filtered and concentrated. 17.17 g (88.4 mmol, corresponding to 63% of theor.) of the product is obtained.

Workup

  1. temperaturethe mixture is cooled to room temperature
  2. extractionextracted with chloroform
  3. extractionextracted with DCM
  4. washThe combined organic phases are washed with saturated NaCl solution
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custom17.17 g (88.4 mmol, corresponding to 63% of theor.) of the product is obtained

Sources & evidence

ORD record
ord-692fa87441cb477a8e2d3081c0f0bc96
Source dataset
uspto-grants-2013_09
Patent number
US08524724B2

Linked notes

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