4-Nitrobenzaldehyde → HCID 178433955, compound

HRID 1762384Notes

Reaction equation

HRID 1762384 reaction equation
[Cl-:1].[NH2:2][N+:3]1[CH:7]=[CH:6][N:5]([N:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]([CH3:18])[CH3:17])=[CH:12][CH:11]=2)[C:4]=1[CH3:19].[N+:20]([C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1)([O-:22])=[O:21]>C(O)(=O)C>[Cl-:1].[CH3:17][N:16]([CH3:18])[C:13]1[CH:14]=[CH:15][C:10]([CH:9]=[N:8][N+:5]2[CH:6]=[CH:7][N:3]([N:2]=[CH:27][C:26]3[CH:29]=[CH:30][C:23]([N+:20]([O-:22])=[O:21])=[CH:24][CH:25]=3)[C:4]=2[CH3:19])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 70351310HCID 70351310, compound

Product 1

HCID 178433955HCID 178433955, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

56 mg (0.2 mmol) of 1-amino-3-[[p-(dimethylamino)-benzylidene]amino]-2-methylimidazolium chloride and 30 mg (0.2 mmol) of p-nitrobenzaldehyde are dissolved in 5 ml of glacial acetic acid. After 2 days the solution is evaporated, and the residue is chromatographed on 5 g of silica gel (particle size 0.063-0.200 mm) while eluting chloroform/methanol (87:13) and recrystallized from methylene chloride/petroleum ether. There is obtained 1-[[p-(dimethylamino)benzylidene]amino]-2-methyl-3-[[p-nitrobenzylidene]amino]-imidazolium chloride of melting point 252° (decomposition).

Workup

  1. customAfter 2 days the solution is evaporated
  2. customthe residue is chromatographed on 5 g of silica gel (particle size 0.063-0.200 mm)
  3. washwhile eluting chloroform/methanol (87:13)
  4. customrecrystallized from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-ed28c1c9628548cba0235cde965bf5d7
Source dataset
uspto-grants-1989_05
Patent number
US04831151

Reaction notes

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