1,2-Dibromoethane → N-Allyl-N-(2-bromo-ethyl)-2-nitro-benzenesulfonamide

HRID 2190181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2190181
[CH2:1]([NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])(=[O:7])=[O:6])[CH:2]=[CH2:3].[Br:17][CH2:18][CH2:19]Br>CN(C=O)C>[CH2:1]([N:4]([CH2:19][CH2:18][Br:17])[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])(=[O:7])=[O:6])[CH:2]=[CH2:3]

Komponenten

4

Edukt 2

HCID 78391,2-DibromoethaneHCID 22739612-nitro-N-prop-2-enylbenzenesulfonamide

Produkt 1

HCID 58052488N-Allyl-N-(2-bromo-ethyl)-2-nitro-benzenesulfonamideAusbeute 48,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N-Allyl-2-nitro-benzenesulfonamide (570 mg, 2.35 mmol) is dissolved in DMF (5 mL) and then CsCO3 (920 mg, 2.82 mmol) and 1,2-dibromoethane (884 mg, 4.71 mmol) is added. The mixture is then microwaved for 30 min at 150° C., then filtered and the solid washed with EtOAc (30 mL). The organic is washed with Brine (20 mL) and then dried over Na2SO4 and then concentrated to dryness. HPLC (CH3CN/H2O/0.1% TFA) provides N-Allyl-N-(2-bromo-ethyl)-2-nitro-benzenesulfonamide (400 mg, 48%). MS-ES [M+H]+=351.1.

Aufarbeitung

  1. customThe mixture is then microwaved for 30 min at 150° C.
  2. filtrationfiltered
  3. washthe solid washed with EtOAc (30 mL)
  4. washThe organic is washed with Brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-7ca97fd2748247cd82fe1002006e0123
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324239B2

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