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

HRID 864547ノート

反応式

HRID 864547 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 313Hydrochloric Acid溶媒HCID 6342Acetonitrile溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-573fe2a24b5349b8a4ae72956017bc21
出典データセット
uspto-grants-1996_10
特許番号
US05563166

反応ノート

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