Acetic Acid → HCID 14404122, compound

HRID 465506Notes

Reaction equation

HRID 465506 reaction equation
C(OO)(=[O:3])C.C(O)(=O)C.[CH:10]1[C:23]2[CH:22]=[C:21]([S:24][CH2:25][N+:26]([O-:28])=[O:27])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1.[OH2:29]>C(Cl)(Cl)Cl>[CH:10]1[C:23]2[CH:22]=[C:21]([S:24]([CH2:25][N+:26]([O-:28])=[O:27])(=[O:3])=[O:29])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 6585Peracetic AcidHCID 14404129HCID 14404129, compound

Product 1

HCID 14404122HCID 14404122, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of peracetic acid in acetic acid (32 wt%, 4 ml, 19 mmol) was added dropwise to an efficiently stirred solution of (9-phenanthrylthio)nitromethane (A) (1 g, 3.7 mmol) in chloroform (50 ml). The mixture was stirred for 20 hours and then diluted with water (20 ml). The organic phase was separated and washed with an aqueous solution of sodium metabisulphite, then with brine, and dried (N2SO4). The solvent was removed by evaporation to give a yellow solid. This was purified by flash chromatography on silica (Merck Kieselgel Art. 7736) eluting with toluene to give (9-phenanthrylsulphonyl)nitromethane, as a white crystalline solid (180 mg, 16% yield) m.p. 165°-166° C., (after recrystallisation from toluene); microanalysis, found: C, 59.7; H, 3.7; N, 4.6%; C15H11NO4S requires: C, 59.8; H, 3.7; N, 4.7%

Workup

  1. customThe organic phase was separated
  2. washwashed with an aqueous solution of sodium metabisulphite
  3. dry with materialwith brine, and dried (N2SO4)
  4. customThe solvent was removed by evaporation
  5. customto give a yellow solid
  6. customThis was purified by flash chromatography on silica (Merck Kieselgel Art. 7736)
  7. washeluting with toluene

Sources & evidence

ORD record
ord-1fa46703b2dc4189b4116656b6db1258
Source dataset
uspto-grants-1992_10
Patent number
US05153227

Reaction notes

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