Diisopropylethylamine → 1-[2-(5,6-Difluorobenzimidazol-2-ylthio)ethyl]-4-formylpiperazine

HRID 1354252ノート

反応式

HRID 1354252 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[C:22]([F:23])=[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:23][C:22]1[C:13]([F:12])=[CH:14][C:15]2[N:19]=[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:17][C:16]=2[CH:21]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 99422134-(2-Hydroxyethyl)piperazine-1-carbaldehydeHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 106791065,6-difluoro-1H-benzimidazole-2-thiol

生成物 1

HCID 231161611-[2-(5,6-Difluorobenzimidazol-2-ylthio)ethyl]-4-formylpiperazine収率 78%

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 (1.11 g, 7.0 mmol), 5,6-difluoro-2-mercaptobenzimidazole (1.30 g, 7.0 mmol), and diisopropylethylamine (3.62 g, 28.0 mmol) were dissolved in propionitrile (50 mL), and cyanomethyltrimethylphosphonium iodide (6.80 g, 28.0 mmol) was added thereto, followed by stirring for one hour at 92° C. under argon. The reaction mixture was allowed to cool and then poured in water (100 mL), followed by extraction with chloroform (100 mL×3). The organic layer was washed with saturated brine and then dried over sodium sulfate anhydrate, and the product was concentrated under reduced pressure. The crude product was crystallized from acetone-ether, to thereby yield 1-[2-(5,6-difluorobenzimidazol-2-ylthio)ethyl]-4-formylpiperazine (1.78 g, yield 78%) as a yellow crystalline powder.

後処理

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

出典と根拠

ORDレコード
ord-b548b0fb1a1f4bff9e20d0bb3e68ea7c
出典データセット
uspto-grants-2007_05
特許番号
US07223764B2

反応ノート

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