Hydrogen Peroxide → HCID 18930399, compound

HRID 1464677Notes

Reaction equation

HRID 1464677 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-2649836c343f40d09bb895a15a4ca690
Source dataset
uspto-grants-1994_04
Patent number
US05306827

Reaction notes

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