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

HRID 1354260ノート

反応式

HRID 1354260 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 7854Propionitrile溶媒

反応条件

温度
92 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-27a4d1b7b6ce4a5a8e5779686c918492
出典データセット
uspto-grants-2007_05
特許番号
US07223764B2

反応ノート

読み込み中…