1H-imidazole-2-carbaldehyde → 1-(o-Nitrobenzyl)-imidazole-2-carboxaldehyde

HRID 1739981Notes

Reaction equation

HRID 1739981 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].[N+:8]([C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13]Br)([O-:10])=[O:9]>>[N+:8]([C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7])([O-:10])=[O:9]

Participants

3

Reactant 2

HCID 249551H-imidazole-2-carbaldehydeHCID 77569alpha-Bromo-2-nitrotoluene

Product 1

HCID 127249851-(o-Nitrobenzyl)-imidazole-2-carboxaldehydeYield 94.4%

Procedure

With stirring and external cooling, 4.80 g of 2-imidazolecarboxaldehyde is added and the cooling bath removed. Slight external heating results in a yellow solution. The reaction mixture is chilled in ice and 10.8 g of 2-nitrobenzyl bromide is added. The reaction mixture is stirred at 0° C. for 18 hours. The volatiles are removed in vacuo to a residue which is stirred with ice water, filtered and the cake washed well with water and suction dried to give 10.9 g of the desired product as a solid, m.p. 141-144° C. MH+ 232.

Workup

  1. customthe cooling bath removed
  2. temperatureSlight external heating
  3. customresults in a yellow solution
  4. temperatureThe reaction mixture is chilled in ice
  5. stirringThe reaction mixture is stirred at 0° C. for 18 hours
  6. customThe volatiles are removed in vacuo to a residue which
  7. stirringis stirred with ice water
  8. filtrationfiltered
  9. washthe cake washed well with water and suction
  10. customdried

Sources & evidence

ORD record
ord-4a8d2014e5944140aa808f5bdf64101a
Source dataset
uspto-grants-1999_10
Patent number
US05968930

Reaction notes

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