Nitric Acid → HCID 15291316, compound

HRID 1654482Notes

Reaction equation

HRID 1654482 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+]>S(=O)(=O)(O)O>[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, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

5-Chloro-1-isopropyl-2-(4-methyl-1-piperazinyl)benzimidazole (24.1 g) was dissolved in concentrated sulfuric acid (160 ml). To the solution were added dropwise concentrated nitric acid (7.8 g) and concentrated sulfuric acid (20.2 g) at 0° C. and the mixture was stirred at 0° C. for 5 minutes. 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 to give 5-chloro-1-isopropyl-2-(4-methyl-1-piperazinyl)-6-nitrobenzimidazole (25.5 g). A part of the obtained product was recrystallized from acetonitrile, which showed the physical properties consistent with those in Preparation 8.

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

Sources & evidence

ORD record
ord-6af057016719492e8d22723c5bb26d2e
Source dataset
uspto-grants-1995_04
Patent number
US05407936

Reaction notes

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