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

HRID 374530노트

반응식

HRID 374530 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 313Hydrochloric Acid용매HCID 6342Acetonitrile용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-33bad6dc5b0248fcbf4ffd491146ac7f
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05480902

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