2-Chloro-5,6-dinitrobenzimidazole → HCID 178507223, compound

HRID 2289463Notes

Reaction equation

HRID 2289463 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([N+:14]([O-])=O)=[CH:7][C:5]=2[N:6]=1>CC(O)=O.CCOC(C)=O.[Fe]>[CH:7]1[C:8]([NH2:14])=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=[C:4]2[N:3]=[C:2]([Cl:1])[NH:6][C:5]=12

Participants

5

Reactant 1

HCID 2678102-Chloro-5,6-dinitrobenzimidazole

Product 1

HCID 178507223HCID 178507223, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.213 g (5.0 mmol) of 2-chloro-5,6-dinitrobenzimidazole (22) and 1.398 g (25 mmol) of iron powder in 50 mL of AcOH was stirred at room temperature for 4 h. The reaction mixture was diluted with ~100 mL of EtOAc, filtered, and the solid was washed with portions of EtOAc (total EtOAc used 100 mL). The filtrate and washings were combined and washed with H2O (100 mL×3). The H2O layer was extracted with 100 mL of EtOAc. The EtOAc solutions were combined, evaporated, coevaporated with toluene (10 mL×3), MeOH (10 mL×2) to give a brown solid.

Workup

  1. filtrationfiltered
  2. washthe solid was washed with portions of EtOAc (total EtOAc used 100 mL)
  3. washwashed with H2O (100 mL×3)
  4. extractionThe H2O layer was extracted with 100 mL of EtOAc
  5. customevaporated
  6. customto give a brown solid

Sources & evidence

ORD record
ord-2ba3ab8ac10b44bb83ff1f1460da9690
Source dataset
uspto-grants-2000_07
Patent number
US06093698

Reaction notes

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