N-bromobutanimide → 5-(4'-bromomethylbiphenyl-2-yl)-1-(4-nitrophenyl)-1H-tetrazole

HRID 37616

Reaktionsgleichung

Reaktionsgleichung von HRID 37616
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[N:18]([C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=3)[N:17]=[N:16][N:15]=2)=[CH:4][CH:3]=1.[Br:28]N1C(=O)CCC1=O>CC(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:28][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[N:18]([C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=3)[N:17]=[N:16][N:15]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 199357765-(4'-Methyl[1,1'-biphenyl]-2-yl)-1-(4-nitrophenyl)-1H-tetrazole

Produkt 1

HCID 199357915-(4'-bromomethylbiphenyl-2-yl)-1-(4-nitrophenyl)-1H-tetrazoleAusbeute 79,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6547AzobisisobutyronitrileKatalysatorHCID 62781,1,1-TrichloroethaneLösungsmittel

Versuchsvorschrift

A mixture of compound D (8.0 g; 21 mmol), N-bromosuccinimide (4.53 g; 25 mmol) and azo(bisisobutyronitrile) (73 mg) in methyl chloroform (50 ml) was heated at reflux for 4 hours. The mixture was cooled to ambient temperature, washed with water (3×50 ml), and the suspended solid collected by filtration to give 5-(4'-bromomethylbiphenyl-2-yl)-1-(4-nitrophenyl)-1H-tetrazole (E) (7.3 g), m.p 192°-195° C.; NMR (CDCl3): 4.4(2H, s), 6.52(2H, d), 6.85(2H, d), 7.07(2H, d), 7.4(1H, d), 7.7(2H, m), 7.9(1H, d).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. washwashed with water (3×50 ml)
  4. filtrationthe suspended solid collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-df9997b1aa1e4db888a9ab3bcd42ebcb
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420292

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