2-Cyano-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-4-nitrobenzenesulfonamide → HCID 67173422, Verbindung

HRID 1256134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256134
[C:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[S:12]([NH:15][C:16]1[CH:17]=[CH:18][C:19]2[CH2:23][O:22][B:21]([OH:24])[C:20]=2[CH:25]=1)(=[O:14])=[O:13])#[N:2]>CO.[NH4+].[OH-].[Ni]>[NH2:9][C:7]1[CH:6]=[CH:5][C:4]([S:12]([NH:15][C:16]2[CH:17]=[CH:18][C:19]3[CH2:23][O:22][B:21]([OH:24])[C:20]=3[CH:25]=2)(=[O:13])=[O:14])=[C:3]([CH2:1][NH2:2])[CH:8]=1

Komponenten

4

Edukt 1

HCID 671740652-Cyano-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-4-nitrobenzenesulfonamide

Produkt 1

HCID 67173422HCID 67173422, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 21894508Ammonium hydroxide methanolLösungsmittel

Versuchsvorschrift

To a solution of 2-cyano-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-4-nitrobenzenesulfonamide (1.077 g, 3 mmol) in MeOH/NH4OH (100 ml/10 ml) was added Raney Ni (2 g) under nitrogen, then the solution was stirred under hydrogen atmosphere at room temperature for overnight. The mixture was filtered and the filtrate was concentrated to give title compound 4-amino-2-(aminomethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide (1.0 g, 100%) as a green solid. 1H NMR: DMSO 400 MHz. δ7.41 (d, J=14.0 Hz, 2H), 7.16 (d, J=8.0 Hz, 1H), 7.08 (d, J=8.0 Hz, 1H), 6.63 (s, 1H), 6.33 (d, J=8.4 Hz, 1H), 5.82 (brs, 2H), 4.84 (s, 2H), 3.95 (s, 2H).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-bebd910f8da044c7b1d4ccbc4244f64b
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461134B2

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