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

HRID 352793ノート

反応式

HRID 352793 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-949ae94802f847f6afe43a91cbb0645e
出典データセット
uspto-grants-2004_06
特許番号
US06747023B1

反応ノート

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