Potassium peroxymonosulphate → HCID 19900832, compound

HRID 1029762Notes

Reaction equation

HRID 1029762 reaction equation
S([O-])(O[O-])(=O)=[O:2].[K+].[K+].[CH3:9][C:10]1[C:11]2[CH:18]=[CH:17][CH:16]=[C:15]([S:19][CH2:20][N+:21]([O-:23])=[O:22])[C:12]=2[S:13][CH:14]=1>O.COCCOC>[CH3:9][C:10]1[C:11]2[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH2:20][N+:21]([O-:23])=[O:22])=[O:2])[C:12]=2[S:13][CH:14]=1

Participants

5

Reactant 2

HCID 10313463Potassium peroxymonosulphateHCID 19900804HCID 19900804, compound

Product 1

HCID 19900832HCID 19900832, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
5 °C

Procedure

A solution of potassium peroxymonosulphate (`oxane` trade mark; 1.0 g, 1.63 mmol) in water (20 ml) was added in one portion to a stirred solution of 3-methyl-7-(nitromethylthio)benzo[b]thiophene (0.7 g, 2.93 mmol) in 1,2-dimethoxyethane (40 ml) cooled to 5° C. The mixture was allowed to warm to ambient temperature and stirred for 18 hours. The reaction mixture was diluted with water (50 ml) and extracted with ethyl acetate (3×50 ml). These extracts were washed with water, dried (MgSO4), and evaporated to leave an oil, which was purified by flash chromatography using 4:1 v/v dichloromethane/hexane as eluant, to give 3-methyl-7-(nitromethylsulphinyl)benzo[b]thiophene as a pale yellow solid (0.35 g); NMR:2.5(s, 3H), 5.55(s, 2H), 7.25(s, 1H), 7.6-8.0(m, 3H).

Workup

  1. temperatureto warm to ambient temperature
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washThese extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto leave an oil, which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-96e7ec332d6741b0b5e9a2cb24adf204
Source dataset
uspto-grants-1992_04
Patent number
US05102905

Reaction notes

Loading…