Triethylamine → N-2-(4-bromophenyl)ethyl 2-propanesulfonamide

HRID 380969

Reaktionsgleichung

Reaktionsgleichung von HRID 380969
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:18]([S:21](Cl)(=[O:23])=[O:22])([CH3:20])[CH3:19]>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH:8][S:21]([CH:18]([CH3:20])[CH3:19])(=[O:23])=[O:22])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 533915p-Bromophenethylamine

Produkt 1

HCID 21893403N-2-(4-bromophenyl)ethyl 2-propanesulfonamideAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 10.0 g (50 mmol) of 4-bromophenethylamine and 7.6 mL (55 mmol) of triethylamine in 150 mL of dichloromethane was added a solution of 6.2 mL (55 mmol) of isopropylsulfonyl chloride in 40 mL of dichloromethane dropwise. The mixture was stirred at room temperature for 18 hr. The mixture was washed with 100 mL of 1N aqueous hydrochloric acid, the organic layer was separated and the aqueous layer extracted one time with 100 mL each of dichloromethane. The combined organics were dried (Na2SO4), filtered and concentrated in vacuo to afford 6.7 g (44%) of the title compound.

Aufarbeitung

  1. washThe mixture was washed with 100 mL of 1N aqueous hydrochloric acid
  2. customthe organic layer was separated
  3. extractionthe aqueous layer extracted one time with 100 mL each of dichloromethane
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4961eb21f1a44991b76309d27faacb18
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303816B1

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