Water → 3-(4-(methylsulfonamido)phenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate

HRID 1188259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1188259
[F:1][C:2]([F:26])([F:25])[S:3]([O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:24])[C:12]([C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=3)=[CH:13][O:14]2)=[CH:9][CH:8]=1)(=[O:5])=[O:4].[CH3:27][S:28](Cl)(=[O:30])=[O:29].O>N1C=CC=CC=1>[F:26][C:2]([F:1])([F:25])[S:3]([O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:24])[C:12]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][S:28]([CH3:27])(=[O:30])=[O:29])=[CH:19][CH:18]=3)=[CH:13][O:14]2)=[CH:9][CH:8]=1)(=[O:5])=[O:4]

Komponenten

5

Edukt 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 866950533-(4-aminophenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate

Produkt 1

HCID 866950543-(4-(methylsulfonamido)phenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonateAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a suspension of 3-(4-aminophenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate (2.2 g, 7.12 mmol) in pyridine (10 mL) at 0° C. was added methanesulfonyl chloride (1.1 mL, 14.24 mmol) over 5 minutes, and then warmed up to room temperature under stirring conditions. After 2 hours the reaction was complete, and water was added in portions under vigorous stirring. The organic phase was then separated and concentrated and the resulting solids were filtered and dried under high vacuum. The solids were heated in acetonitrile, stirred until room temperature was achieved, then filtered off to give 3-(4-(methylsulfonamido)phenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate (2.49 g). 1H NMR (DMSO, 400 MHz) δ 9.87 (s, 1H); 8.60 (s, 1H); 8.31 (d, J=8.0 Hz, 1H); 8.09 (s, 1H); 7.65 (d, J=8.0 Hz, 1H); 7.57 (d, J=8.4 Hz, 2H); 7.27 (d, J=8.4 Hz, 2H); 3.01 (s, 3 H).

Aufarbeitung

  1. customThe organic phase was then separated
  2. concentrationconcentrated
  3. filtrationthe resulting solids were filtered
  4. customdried under high vacuum
  5. temperatureThe solids were heated in acetonitrile
  6. filtrationfiltered off

Quellen und Nachweise

ORD-Eintrag
ord-75a08bd057c14a8cbbb22db506baacef
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673966B2

Notizen zur Reaktion

Wird geladen…