Methanesulfonyl chloride → N-[5-(Methanesulfonylamino-methyl)-naphthalen-2-yl]-benzenesulfonamide

HRID 492097

Reaktionsgleichung

Reaktionsgleichung von HRID 492097
[NH2:1][CH2:2][CH:3]1[CH2:12][CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:6]=[CH:5][C:4]1=2.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl.N1C=CC=CC=1>[CH3:23][S:24]([NH:1][CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([NH:13][S:14]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)(=[O:16])=[O:15])=[CH:8]2)(=[O:26])=[O:25]

Komponenten

5

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 57678964N-(5-aminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide

Produkt 1

HCID 57678989N-[5-(Methanesulfonylamino-methyl)-naphthalen-2-yl]-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-(5-Aminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide is dissolved in methylene chloride and pyridine, and the mixture is cooled in an ice bath. Methanesulfonyl chloride is added dropwise, and the reaction mixture is stirred at ice bath temperature, then allowed to warm to room temperature. The reaction mixture is quenched by addition of water and extracted with methylene chloride. The organic layer is washed with water, dried (MgSO4), filtered and concentrated under reduced pressure to give N-[5-(Methanesulfonylamino-methyl)-naphthalen-2-yl]-benzenesulfonamide. 5-(Methanesulfonylamino-methyl)-naphthalene-2-sulfonic acid phenylamide may be similarly prepared.

Aufarbeitung

  1. customThe reaction mixture is quenched by addition of water
  2. extractionextracted with methylene chloride
  3. washThe organic layer is washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1f95af295ef4496ea09dfb8cac524b85
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531577B2

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