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

HRID 1900115Notes

Reaction equation

HRID 1900115 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

15 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-50995d8c848d4651a70ca341a0f0669b
Source dataset
uspto-grants-1996_11
Patent number
US05574058

Reaction notes

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