Water → S-Methyl-S-(4-nitrophenyl)sulfoximine

HRID 1891061Notes

Reaction equation

HRID 1891061 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.O>C(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

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 3058821-(Methylsulfinyl)-4-nitrobenzene

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

1.56 g (8.5 mmol) of 1-(methylsulfinyl)-4-nitrobenzene in 20 ml of DCM is mixed with 0.70 g (9.5 mmol) of sodium azide. The batch is slowly mixed at 0° C. with 2.3 ml of concentrated sulfuric acid and then heated to 45° C. After 16 hours, the batch is cooled to room temperature, mixed with water and extracted from DCM. The aqueous phase is set at pH 11 with 15% NaOH solution and extracted from DCM. The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. 1.08 g (5.4 mmol, corresponding to 63% of theory) of the product is obtained.

Workup

  1. temperaturethe batch is cooled to room temperature
  2. extractionextracted from DCM
  3. extractionextracted from DCM
  4. dry with materialThe combined organic phases are dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. custom1.08 g (5.4 mmol, corresponding to 63% of theory) of the product is obtained

Sources & evidence

ORD record
ord-a951a21b77544ae898d8390d06226a56
Source dataset
uspto-grants-2013_08
Patent number
US08507510B2

Reaction notes

Loading…