N-tert-butyl-3-chloropropane-1-sulfonamide → N-tert-Butylcyclopropanesulfonamide

HRID 339156

Reaktionsgleichung

Reaktionsgleichung von HRID 339156
[C:1]([NH:5][S:6]([CH2:9][CH2:10][CH2:11]Cl)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC>C1COCC1>[C:1]([NH:5][S:6]([CH:9]1[CH2:11][CH2:10]1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 11701296N-tert-butyl-3-chloropropane-1-sulfonamideHCID 178418339Butyllithium

Produkt 1

HCID 22499301N-tert-ButylcyclopropanesulfonamideAusbeute 56,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of N-tert-butyl-(3-chloro)propylsulfonamide (2.14 g, 10.0 mmol) in THF (100 mL) was added n-BuLi (2.5 M in hexane, 8.0 mL, 20.0 mmol) at −78° C. The reaction mixture was allowed to warm up to room temperature over period of 1 h. The volatiles were removed in vacuo. The residue was partitioned between EtOAC and water (200 mL, 200 mL). The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from hexane to yield the desired product as a white solid (1.0 g, 56%).

Aufarbeitung

  1. customThe volatiles were removed in vacuo
  2. customThe residue was partitioned between EtOAC and water (200 mL, 200 mL)
  3. washThe separated organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-5f0473953fab46668f705a9dd975081f
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889871B2

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