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5-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride → HCID 18180112, Verbindung

HRID 1358960
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1358960
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:16])[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]1.[Cl:17][C:18]1[CH:31]=[CH:30][C:21]2[S:22][C:23]([S:26](Cl)(=[O:28])=[O:27])=[C:24]([CH3:25])[C:20]=2[CH:19]=1>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:16][S:26]([C:23]2[S:22][C:21]3[CH:30]=[CH:31][C:18]([Cl:17])=[CH:19][C:20]=3[C:24]=2[CH3:25])(=[O:28])=[O:27])[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]1
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Komponenten

4

Edukt 2

HCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chlorideHCID 118447613-Methoxy-4-(4-methylpiperazin-1-yl)aniline

Produkt 1

HCID 18180112HCID 18180112, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 3-methoxy-4-(4-methylpiperazin-1-yl)phenylamine (D35) (50 mg, 0.23 mmol) and 5-chloro-3-methylbenzo[b]thiophene-2-sulfonyl chloride (64 mg, 0.23 mmol) in dichloromethane (2 ml) was allowed to stand at room temperature overnight. The reaction mixture was diluted with dichloromethane and washed with potassium carbonate (aq), which was back-extracted with further dichloromethane. The combined organic phases were dried (Na2SO4) and evaporated under reduced pressure to give a crude product, which was purified by chromatography on silica gel, eluting with methanol and dichloromethane. This gave the title compound (E128) as an off-white solid (36 mg, 34%) MH+=466.

Aufarbeitung

  1. washwashed with potassium carbonate (aq), which
  2. extractionwas back-extracted with further dichloromethane
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customto give a crude product, which
  6. customwas purified by chromatography on silica gel
  7. washeluting with methanol and dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-e63ee4a5cb2449c883e15be37e900b42
Quelldatensatz
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06599904B2

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