Benzyl Alcohol → 1-(Phenoxymethyl)-2-sulfamoylbenzene

HRID 553468

Reaktionsgleichung

Reaktionsgleichung von HRID 553468
C(O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[S:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1F)(=[O:14])(=[O:13])[NH2:12].Cl.CN([CH:26]=[O:27])C>>[O:27]([CH2:26][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[S:11](=[O:14])(=[O:13])[NH2:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 5

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 1936632-Fluorobenzenesulfonamide

Produkt 1

HCID 669154671-(Phenoxymethyl)-2-sulfamoylbenzeneAusbeute 66,7 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of benzyl alcohol (1 g, 8.6 mmol) in 10 mL of dry DMF was added to NaH (0.7 g, 17.1 mmol.) at 0° C. The reaction mixture was stirred at 0° C. for 30 min under N2. To the resulting mixture was added 2-sulfamoyl fluorobenzene (1 g, 5.7 mmol.) in 20 mL of dry DMF. The reaction mixture was stirred at 80-90° C. for 3 hours. After cooling to r.t., the reaction mixture was poured into ice-water and neutralized with aq. HCl (2 M) to pH 7. The mixture was extracted with ethyl acetate (3×50 mL). The combined organic layer was over Na2SO4, filtered and concentrated to afford crude 1-(phenoxymethyl)-2-sulfamoylbenzene (1 g, 66.7%), which was used directly without further purification.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 80-90° C. for 3 hours
  2. temperatureAfter cooling to r.t.
  3. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c69de01c598c4e36910f9f6ff46cc8f6
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048862B2

Verknüpfte Notizen

Wird geladen…