Fuming sulfuric acid → Ethyl(imino)(4-nitrophenyl)-_6-sulfanone

HRID 1027857Notes

Reaction equation

HRID 1027857 reaction equation
OS(O)(=O)=O.O=S(=O)=O.[CH2:10]([S:12]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:13])[CH3:11].[N-:23]=[N+]=[N-].[Na+].C(=O)([O-])O.[Na+]>>[CH2:10]([S:12]([C:14]1[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=1)(=[NH:23])=[O:13])[CH3:11]

Participants

5

Reactant 4

HCID 24681Fuming sulfuric acidHCID 33557Sodium AzideHCID 2791461-(Ethylsulfinyl)-4-nitrobenzeneHCID 516892Sodium Bicarbonate

Product 1

HCID 59550863Ethyl(imino)(4-nitrophenyl)-_6-sulfanoneYield 89%

Conditions

Temperature
45 °C

Procedure

30.5 ml of oleum (20% SO3) was added carefully, on an ice bath, to 6.00 g (30.12 mmol) of (RS)-1-ethylsulfinyl-4-nitrobenzene. Then, under argon, 2.35 g (36.14 mmol) of sodium azide was added carefully, in portions and with stirring, and the mixture was then heated to 45° C. After 6 hours the mixture was cooled to room temperature and carefully poured onto ice. The mixture was alkalized with sodium hydrogencarbonate and was extracted with ethyl acetate (2×). The combined organic phases were dried (Na2SO4), filtered and concentrated by evaporation. 5.74 g (26.79 mmol; yield: 89%) of the product was obtained.

Workup

  1. temperatureAfter 6 hours the mixture was cooled to room temperature
  2. additioncarefully poured onto ice
  3. extractionwas extracted with ethyl acetate (2×)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. custom5.74 g (26.79 mmol; yield: 89%) of the product was obtained

Sources & evidence

ORD record
ord-e5ab2fe563a6422eaa442681c1eb7524
Source dataset
uspto-grants-2014_05
Patent number
US08735412B2

Reaction notes

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