Dimethylformamide → 4-(4-Fluorophenoxy)benzenesulphonyl chloride

HRID 1953824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1953824
[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13](O)(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[Na].S(Cl)([Cl:22])=O.CN(C)C=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13]([Cl:22])(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 5360545SodiumHCID 110225964-(4-fluorophenoxy)benzenesulfonic Acid

Produkt 1

HCID 27827574-(4-Fluorophenoxy)benzenesulphonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a slurry of 15.0 g (0.052 mol) of 4-(4-fluorophenoxy)benzenesulfonic acid □, sodium salt, in 150 mL of dry toluene was added 11.3 mL (0.155 mol, 3 equivalents) of thionyl chloride and 0.04 mL (0.5 mmol, 0.01 equivalents) of dimethylformamide. The resulting mixture was stirred at room temperature for 48 hours, filtered through diatomaceous earth, and concentrated under reduced pressure to 40 mL. This solution was used without further purification to prepare 1-[4-(4-fluorophenoxy)benzenesulfonylamino] cyclopentanecarboxylic acid benzyl ester.

Aufarbeitung

  1. filtrationfiltered through diatomaceous earth
  2. concentrationconcentrated under reduced pressure to 40 mL
  3. customThis solution was used without further purification
  4. customto prepare 1-[4-(4-fluorophenoxy)benzenesulfonylamino] cyclopentanecarboxylic acid benzyl ester

Quellen und Nachweise

ORD-Eintrag
ord-370edf3c9bd74491bf80c7e0fa60e866
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06118016

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