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

HRID 1354252노트

반응식

HRID 1354252 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[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 7854Propionitrile용매

반응 조건

온도
92 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b548b0fb1a1f4bff9e20d0bb3e68ea7c
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223764B2

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