Nitric Acid → HCID 15291316, compound

HRID 1654481Notes

Reaction equation

HRID 1654481 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]([CH:16]([CH3:18])[CH3:17])[C:7]([N:9]3[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]3)=[N:8][C:4]=2[CH:3]=1.[N+:21]([O-])([OH:23])=[O:22].O.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:5]2[N:6]([CH:16]([CH3:18])[CH3:17])[C:7]([N:9]3[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]3)=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 20078040HCID 20078040, compound

Product 1

HCID 15291316HCID 15291316, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

5-Chloro-1-isopropyl-2-(4-methyl-1-piperazinyl)benzimidazole (2.7 g) was dissolved in acetic acid (15 ml). To the solution was added fuming nitric acid (3 ml) at 0° C. and then the mixture was stirred at 60° C. for 1 hour. The reaction mixture was poured into water and the mixture was made basic with an aqueous sodium hydroxide solution and extracted with chloroform. The chloroform layer was washed with water and dried over anhydrous magnesium sulfate and then the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography [eluted with chloroform-methanol (10:1, v/v)] to give 5-chloro-1-isopropyl-2-(4-methyl-1-piperazinyl)-6-nitrobenzimidazole (1.8 g). A part of the obtained product was recrystallized from acetonitrile, which showed the following physical properties:

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. washeluted with chloroform-methanol (10:1

Sources & evidence

ORD record
ord-6dfa37a4c8ec4edd807376a11b93b82f
Source dataset
uspto-grants-1995_04
Patent number
US05407936

Reaction notes

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