Water → 5,7-Dimethyl-6-(nitromethylsulphonyl)thiachroman-1,1-dioxide

HRID 2081811Notes

Reaction equation

HRID 2081811 reaction equation
C(OO)(=[O:3])C.[CH3:6][C:7]1[C:16]([S:17][CH2:18][N+:19]([O-:21])=[O:20])=[C:15]([CH3:22])[CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][CH2:11]S2.S([S:27]([O-:29])=[O:28])([O-])(=O)=O.[Na+].[Na+].[OH2:32]>C(O)(=O)C.C(Cl)(Cl)Cl>[CH3:6][C:7]1[C:16]([S:17]([CH2:18][N+:19]([O-:21])=[O:20])(=[O:3])=[O:32])=[C:15]([CH3:22])[CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][CH2:11][S:27]2(=[O:28])=[O:29]

Participants

7

Reactant 4

HCID 962WaterHCID 6585Peracetic Acid2×HCID 656671Sodium PyrosulfiteHCID 570022415,7-Dimethyl-6-(nitromethylthio)thiachroman

Product 1

HCID 678275245,7-Dimethyl-6-(nitromethylsulphonyl)thiachroman-1,1-dioxideYield 47%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

A 35% w/v solution of peracetic acid in acetic acid (3.2 ml) was added in a slow stream to a stirred solution of 5,7-dimethyl-6-(nitromethylthio)thiachroman (500 mg, 1.86 mM) in chloroform (25 ml). The solution was then stirred and heated at 60° C. Two further quantities of 35% w/v peracetic acid solution (3.2 ml) were added after 2 hours and 3.5 hours, respectively. After 7.5 hours, the reaction mixture was cooled and a solution of sodium metabisulphite (5 g) in water (50 ml) was added slowly with further cooling. The organic layer was separated and the aqueous layer extracted with chloroform. The combined extracts were dried (Na2SO4) and evaporated. The white solid obtained was recrystallised from toluene to give 5,7-dimethyl-6-(nitromethylsulphonyl)thiachroman-1,1-dioxide (290 mg, 47% yield), m.p. 168°-170° C.; NMR: (d6 -DMSO): 2.38(2H,m), 2.56(3H,s), 2.65(3H,s), 2.91(2 H,t), 3.55(2H,m), 6.65(2H,s), 7.79(1H,s); microanalysis, found: C,43.3; H,4.1; N,4.1%; C12H15NO6S2 requires: C,43.2; H,4.5; N,4.2%.

Workup

  1. additionwere added after 2 hours and 3.5 hours
  2. temperaturethe reaction mixture was cooled
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with chloroform
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. customevaporated
  7. customThe white solid obtained
  8. customwas recrystallised from toluene

Sources & evidence

ORD record
ord-a27c45b85b314295a943e569c2ebd66b
Source dataset
uspto-grants-1993_02
Patent number
US05185452

Reaction notes

Loading…