2-Chlorobenzenesulfonyl chloride → N-(5-bromo-thiophen-2-ylmethyl)-2-chloro-benzenesulfonamide

HRID 1665010

Reaktionsgleichung

Reaktionsgleichung von HRID 1665010
[Br:1][C:2]1[S:6][C:5]([CH2:7][NH2:8])=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16](Cl)(=[O:18])=[O:17].C(N(CC)C(C)C)(C)C>ClCCl>[Br:1][C:2]1[S:6][C:5]([CH2:7][NH:8][S:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[Cl:9])(=[O:18])=[O:17])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 23130577(5-Bromothiophen-2-yl)methanamine

Produkt 1

HCID 35408985N-(5-bromo-thiophen-2-ylmethyl)-2-chloro-benzenesulfonamideAusbeute 43,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred suspension of 1-(5-bromo-2-thienyl)methanamine (1.00 g) in dichloromethane (15 mL) were slowly added 2-chlorobenzenesulfonyl chloride (1.18 g) and N,N-diisopropyl ethyl amine (0.76 g) at 0° C. After 15 min the ice bath was removed and the mixture was stirred at r.t. for 1.5 h. The mixture was diluted with dichloromethane and washed with 0.5 M HCl and with water. The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure. The product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 95:5 to ethyl acetate) to give N-(5-bromo-thiophen-2-ylmethyl)-2-chloro-benzenesulfonamide (0.83 g) as a colorless solid. MS: 363.9 ([M−H]−)

Aufarbeitung

  1. customat 0° C
  2. customAfter 15 min the ice bath was removed
  3. additionThe mixture was diluted with dichloromethane
  4. washwashed with 0.5 M HCl and with water
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 95:5 to ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-7e0bb01514dc415b93d1ff57b31235ce
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039493B2

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