N-bromobutanimide → 2-(1 Bromobutyl)imidazole

HRID 36988Notes

Reaction equation

HRID 36988 reaction equation
[CH2:1]([C:5]1[N:6](CC2C=CC=CC=2Cl)[C:7](C=O)=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:20][CH:1]([C:5]1[NH:6][CH:7]=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 101075301H-Imidazole-5-carboxaldehyde, 2-butyl-1-[(2-chlorophenyl)methyl]-

Product 1

HCID 199367312-(1 Bromobutyl)imidazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-carboxaldehyde and N-bromosuccinimide in carbon tetrachloride was irradiated to give the 2-(1-bromobutyl)imidazole which was dehydrobrominated by treating 1,8-diazabicyclo[4.5.0]undec-1-ene in tetrahydrofuran to give 2-(1-butenyl)-1-(2-chlorophenyl)methyl-1H-imidazol-5-carboxaldehyde.

Workup

  1. customwas irradiated

Sources & evidence

ORD record
ord-c3b5849743fa40059e35d58d328aede0
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Reaction notes

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