Triethylamine → 3-(5-Bromo-3-thienyl)-5-(p-chlorophenyl)-2-(trifluoromethyl)pyrrole

HRID 2396548Notes

Reaction equation

HRID 2396548 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[S:13][CH:12]=[C:11]([CH:14]([C:19]2([C:32]([F:35])([F:34])[F:33])[N:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[C:21](=O)O2)C[N+]([O-])=O)[CH:10]=1.CCCCCC.C(OCC)(=O)C>C(#N)C.Cl.ClCCCl>[Br:8][C:9]1[S:13][CH:12]=[C:11]([C:14]2[CH:21]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[NH:23][C:19]=2[C:32]([F:35])([F:33])[F:34])[CH:10]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 194192982-[1-(5-Bromo-3-Thienyl)-2-Nitroethyl]-4-(p-Chlorophenyl)-2-(Trifluoromethyl)-3-Oxazolin-5-OneHCID 21226206Ethyl acetate hexane

Product 1

HCID 194192773-(5-Bromo-3-thienyl)-5-(p-chlorophenyl)-2-(trifluoromethyl)pyrrole

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent2×

Procedure

A solution of triethylamine (3.24 g, 32.1 mmol) in acetonitrile is added slowly to a solution of 2-[1-(5-bromo-3-thienyl)-2-nitroethyl]-4-(p-chlorophenyl)-2-(trifluoromethyl)-3-oxazolin-5-one (13.30 g, 26.8 mmol) in acetonitrile. The reaction mixture is stirred at room temperature for several minutes and diluted with dilute hydrochloric acid. The organic layer is separated, dried over MgSO4 and concentrated in vacuo to obtain a black residue. Column chromatography of the residue using silica gel and a (9:1) hexane/ethyl acetate solution gives several solids. One of the solids is stirred in cold 1,2-dichloroethane, filtered and dried to give 3-(5-bromo-3-thienyl)-5-(p-chlorophenyl)-2-(trifluoromethyl) pyrrole as a light tan solid, mp 112°-115° C. Another solid is diluted with hexane and the mixture is refluxed, cooled to room temperature and filtered to obtain 3-(5-bromo-3-thienyl)-5-(p-chlorophenyl)-4-nitro-2-(trifluoromethyl)pyrrole as a yellow solid, mp 174°-176° C.

Workup

  1. customThe organic layer is separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto obtain a black residue
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-1d72b49765434a44bf6b97a5108752be
Source dataset
uspto-grants-1996_02
Patent number
US05492925

Reaction notes

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