Sodium Chloride → 4-(4-Bromobenzylidene)-1-[(6-chlorobenzo[b]thien-2-yl)sulfonyl]piperidine

HRID 352793노트

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HRID 352793 반응식
[Br-].[Br:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.[H-].[Na+].[Cl:31][C:32]1[CH:33]=[CH:34][C:35]2[CH:39]=[C:38]([S:40]([N:43]3[CH2:48][CH2:47][C:46](=O)[CH2:45][CH2:44]3)(=[O:42])=[O:41])[S:37][C:36]=2[CH:50]=1.[Na+].[Cl-]>O1CCCC1.C(O)C.C(OCC)(=O)C>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[C:46]2[CH2:47][CH2:48][N:43]([S:40]([C:38]3[S:37][C:36]4[CH:50]=[C:32]([Cl:31])[CH:33]=[CH:34][C:35]=4[CH:39]=3)(=[O:41])=[O:42])[CH2:44][CH2:45]2)=[CH:27][CH:28]=1

참가 물질

8

반응물 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 2724858[(4-Bromophenyl)methyl]triphenylphosphanium bromideHCID 227099091-[(6-Chlorobenzo[b]thien-2-yl)sulfonyl]piperidin-4-one

생성물 1

HCID 227106584-(4-Bromobenzylidene)-1-[(6-chlorobenzo[b]thien-2-yl)sulfonyl]piperidine

시약·촉매·용매 3

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

In a mixed solvent of tetrahydrofuran (10 ml) and ethanol (10 ml) was dissolved 4-bromobenzyl triphenylphosphonium bromide (512 mg). The resulting solution was cooled to 0° C., followed by the successive addition of sodium hydride (60% in oil, 40 mg) and 1-[(6-chlorobenzo[b]thien-2-yl)sulfonyl]piperidin-4-one (297 mg). The resulting mixture was stirred at room temperature for 16 hours and at 50° C. for 9 hours. Saturated aqueous NaCl solution and ethyl acetate were added to the reaction mixture to separate the same. The resulting organic layer was dried over anhydrous magnesium sulfate, the filtrate was concentrated and the residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=4:1), whereby the title compound (colorless powder, 133 mg) was obtained.

후처리

  1. customto separate the same
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. concentrationthe filtrate was concentrated
  4. customthe residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=4:1), whereby the title compound (colorless powder, 133 mg)
  5. customwas obtained

출처 및 근거

ORD 기록
ord-949ae94802f847f6afe43a91cbb0645e
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06747023B1

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