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

HRID 352793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 352793
[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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-949ae94802f847f6afe43a91cbb0645e
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06747023B1

Notizen zur Reaktion

Wird geladen…