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

HRID 864547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 864547
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

Komponenten

7

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 313Hydrochloric AcidLösungsmittelHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-573fe2a24b5349b8a4ae72956017bc21
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05563166

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