Hydrogen Peroxide → HCID 18930399, compound

HRID 375205Notes

Reaction equation

HRID 375205 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:18]([F:21])([F:20])[F:19])=[CH:11][C:12]=2[S:13][C:14]([F:17])([F:16])[F:15])=[CH:4][CH:3]=1.OO.C(OCC)(=[O:26])C.[OH2:30]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:18]([F:21])([F:19])[F:20])=[CH:11][C:12]=2[S:13]([C:14]([F:16])([F:17])[F:15])(=[O:26])=[O:30])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide3×HCID 18930386HCID 18930386, compoundHCID 22728543Water ethylacetate

Product 1

HCID 18930399HCID 18930399, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

A solution of 2-(p-chlorophenyl)-5-(trifluoromethyl)-3-[(trifluoromethyl)thio]pyrrole (1.5 g, 4.3 mmol) in acetic acid is treated with hydrogen peroxide (1.5 mL, 30%, 13 mmol), stirred at 95° C. for several hours, treated with additional hydrogen peroxide (1 mL), stirred at 90° C. for four hours, cooled to room temperature, stirred for 48 hours, treated with additional hydrogen peroxide (1 mL), stirred for several hours at reflux, cooled and diluted with an ethyl acetate/water mixture. The organic phase is separated, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain an oil. Crystallization of the oil from petroleum ether gives a white semi-solid which is chromatographed using silica gel and a 1:9 ethyl acetate/hexanes solution to obtain the title product as a white solid (mp 167°-169° C.) which is identified by 1HNMR, 19FNMR and 13CNMR spectral analyses.

Workup

  1. stirringstirred at 90° C. for four hours
  2. temperaturecooled to room temperature
  3. stirringstirred for 48 hours
  4. stirringstirred for several hours
  5. temperatureat reflux
  6. temperaturecooled
  7. customThe organic phase is separated
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customto obtain an oil
  11. customCrystallization of the oil from petroleum ether
  12. customgives a white semi-solid which
  13. customis chromatographed

Sources & evidence

ORD record
ord-481ad34dcdb348b08e2d99351908847e
Source dataset
uspto-grants-1996_01
Patent number
US05484807

Reaction notes

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