Diisopropylethylamine → 1-[2-(5-Fluorobenzimidazol-2-ylthio)ethyl]-4-formylpiperazine

HRID 1354260노트

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HRID 1354260 반응식
[CH:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10]O)[CH2:5][CH2:4]1)=[O:2].[F:12][C:13]1[CH:22]=[CH:21][C:16]2[N:17]=[C:18]([SH:20])[NH:19][C:15]=2[CH:14]=1.C(N(C(C)C)CC)(C)C.[I-].C(C[P+](C)(C)C)#N>C(#N)CC.O>[F:12][C:13]1[CH:22]=[CH:21][C:16]2[N:17]=[C:18]([S:20][CH2:10][CH2:9][N:6]3[CH2:7][CH2:8][N:3]([CH:1]=[O:2])[CH2:4][CH2:5]3)[NH:19][C:15]=2[CH:14]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 34348856-fluoro-1H-benzimidazole-2-thiolHCID 99422134-(2-Hydroxyethyl)piperazine-1-carbaldehydeHCID 10514344(Cyanomethyl)trimethylphosphanium iodide

생성물 1

HCID 231161581-[2-(5-Fluorobenzimidazol-2-ylthio)ethyl]-4-formylpiperazine수율 80%

시약·촉매·용매 2

HCID 962Water용매HCID 7854Propionitrile용매

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온도
92 °C

실험 절차

1-Formyl-4-(2-hydroxyethyl)piperazine (1.20 g, 7.6 mmol), 5-fluoro-2-mercaptobenzimidazole (1.28 g, 7.6 mmol), and diisopropylethylamine (3.93 g, 30.4 mmol) was dissolved in propionitrile (50 mL), and cyanomethyltrimethylphosphonium iodide (7.39 g, 30.4 mmol) was added to the mixture, followed by stirring for one hour at 92° C. under argon. The reaction mixture was allowed to cool and then poured into water (100 mL), followed by extraction with chloroform (100 mL×3) The resultant organic layer was washed with saturated brine and then dried over sodium sulfate anhydrate, followed by concentration under reduced pressure. The crude product was crystallized from acetone-ether, to thereby yield 1-[2-(5-fluorobenzimidazol-2-ylthio)ethyl]-4-formylpiperazine (1.87 g, yield 80%) as a brown crystalline powder.

후처리

  1. temperatureto cool
  2. extractionfollowed by extraction with chloroform (100 mL×3) The resultant organic layer
  3. washwas washed with saturated brine
  4. dry with materialdried over sodium sulfate anhydrate
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe crude product was crystallized from acetone-ether

출처 및 근거

ORD 기록
ord-27a4d1b7b6ce4a5a8e5779686c918492
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223764B2

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