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Hydrogen Peroxide → 2-(p-Chlorophenyl)-5-[(trifluoromethyl)sulfonyl]pyrrole-3-carbonitrile

HRID 1975218
Notes
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Reaction equation

HRID 1975218 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([S:15][C:16]([F:19])([F:18])[F:17])=[CH:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1.OO.C(OCC)(=[O:24])C.[OH2:28]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([S:15]([C:16]([F:17])([F:19])[F:18])(=[O:24])=[O:28])=[CH:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 189303922-(p-Chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole-3-carbonitrileHCID 22728543Water ethylacetate

Product 1

HCID 189304462-(p-Chlorophenyl)-5-[(trifluoromethyl)sulfonyl]pyrrole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2-(p-chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole-3-carbonitrile (0.6 g, 0.002 mol) in acetic acid is treated portionwise with 30% hydrogen peroxide solution (0.6 mL, 0.006 mol), stirred for 11/2 hours at 90° C., treated with additional hydrogen peroxide (0.3 mL, 0.003 mol), stirred for two hours at 90° C., stirred for 16 hours at room temperature and diluted with an ethyl acetate/water mixture. The organic phase is separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a solid. The solid is recrystallized from ethylene dichloride to give the title product as a beige solid (mp 228°-230° C.) which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

  1. stirringstirred for two hours at 90° C.
  2. stirringstirred for 16 hours at room temperature
  3. customThe organic phase is separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a solid
  8. customThe solid is recrystallized from ethylene dichloride

Sources & evidence

ORD record
ord-22be83696fce4fc98275dc00b2a926d5
Source dataset
uspto-grants-1994_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05284863

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes