Triethylamine → 2-(p-Chlorophenyl)-4-phenyl-5-(trifluoromethyl)-3-[(trifluoromethyl)sulfonyl]pyrrole

HRID 375207Notes

Reaction equation

HRID 375207 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2C(=O)O[CH:10]([C:14]([F:17])([F:16])[F:15])[N:9]=2)=[CH:4][CH:3]=1.FC(F)(F)S([C:23]([S:31]([C:34]([F:37])([F:36])[F:35])(=[O:33])=[O:32])=[CH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=O)=O.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10]([C:14]([F:15])([F:16])[F:17])=[C:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:23]=2[S:31]([C:34]([F:35])([F:36])[F:37])(=[O:32])=[O:33])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 110652915(2H)-Oxazolone, 4-(4-chlorophenyl)-2-(trifluoromethyl)-HCID 18930436[2,2-Bis(trifluoromethanesulfonyl)ethenyl]benzene

Product 1

HCID 189304082-(p-Chlorophenyl)-4-phenyl-5-(trifluoromethyl)-3-[(trifluoromethyl)sulfonyl]pyrrole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Procedure

A solution of 4-(p-chlorophenyl)-2-(trifluoromethyl)-3-oxazolin-5-one (1.0 g, 3.8 mmol) and β,β-bis[(trifluoromethyl)sulfonyl]styrene (1.4 g, 3.8 mmol) in dimethylformamide is stirred for two hours at 110° C., treated with triethylamine (0.38 g, 3.8 mmol), stirred for several hours at reflux and diluted with an ethyl acetate/water mixture. The organic phase is separated, washed with water and dilute hydrochloric acid, dried over anhudrous magnesium sulfate and concentrated in vacuo to obtain a residue. Chromatography of the residue using silica gel and a 1:10 ethyl acetate/hexanes solution gives the title product as an amber oil which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

  1. temperatureat reflux
  2. customThe organic phase is separated
  3. washwashed with water and dilute hydrochloric acid
  4. dry with materialdried over anhudrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a residue

Sources & evidence

ORD record
ord-5858474433334a1e95d0355033c61b82
Source dataset
uspto-grants-1996_01
Patent number
US05484807

Reaction notes

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