HCID 44203196, compound → HCID 178507592, compound

HRID 2409244Notes

Reaction equation

HRID 2409244 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[N+:14]([O-])=O)=O>C(O)(=O)C.[Zn]>[Cl:1][C:2]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:3]=1[C:4]1[NH:14][C:8]2[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:7]=2[N:6]=1

Participants

4

Reactant 1

HCID 44203196HCID 44203196, compound

Product 1

HCID 178507592HCID 178507592, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

2-Chloro-N-(5-chloro-2-nitro-phenyl)-5-nitro-benzamide (1.78 g; 5 mmol) was dissolved in glacial acetic acid (30 ml) and heated to 70° C. Zinc powder (3.3 g; 50 mmol) was added portionwise. After 2 hours, the reaction was filtered and the solid washed with acetonitrile. The solvents were evaporated and the residue loaded onto a silica gel chromatography column, using dichloromethane/triethylamine. Elution with 20% ethyl acetate in heptane gave 4-chloro-3-(5-chloro-1H-benzoimidazol-2-yl)-phenylamine as an orange powder (0.22 g, 16%).

Workup

  1. filtrationthe reaction was filtered
  2. washthe solid washed with acetonitrile
  3. customThe solvents were evaporated
  4. washElution with 20% ethyl acetate in heptane

Sources & evidence

ORD record
ord-28b4a588c8084d80a6e5bb78cd8da04b
Source dataset
uspto-grants-2014_08
Patent number
US08815895B2

Reaction notes

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