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

HRID 1741784Notes

Reaction equation

HRID 1741784 reaction equation
[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>ClC(Cl)(Cl)C.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

Participants

5

Reactant 2

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

Product 1

HCID 199357915-(4'-bromomethylbiphenyl-2-yl)-1-(4-nitrophenyl)-1H-tetrazoleYield 74.7%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 62781,1,1-TrichloroethaneSolvent

Procedure

A mixture of compound D (8.0 g; 21 mM), N-bromosuccinimide (4.53 g; 25 mM) and azo(bisisobutyronitrile) (73 mg) in 1,1,1-trichloroethane (methyl chloroform) (50 mL) was heated under 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).

Workup

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

Sources & evidence

ORD record
ord-07e39587bf20404691c1f801612d5c7d
Source dataset
uspto-grants-1994_08
Patent number
US05334718

Reaction notes

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