5,6-Dichloro-2-(4-methoxy-3-nitro-phenyl)-1h-benzoimidazole → 5-(5,6-Dichloro-1H-benzo[d]imidazol-2-yl)-2-methoxyaniline

HRID 25510Notes

Reaction equation

HRID 25510 reaction equation
[Cl:1][C:2]1[C:21]([Cl:22])=[CH:20][C:5]2[NH:6][C:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([N+:17]([O-])=O)[CH:10]=3)=[N:8][C:4]=2[CH:3]=1>[Zn].C(O)(=O)C>[Cl:22][C:21]1[C:2]([Cl:1])=[CH:3][C:4]2[NH:8][C:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([NH2:17])[CH:10]=3)=[N:6][C:5]=2[CH:20]=1

Participants

4

Reactant 1

HCID 225684155,6-Dichloro-2-(4-methoxy-3-nitro-phenyl)-1h-benzoimidazole

Product 1

HCID 225684435-(5,6-Dichloro-1H-benzo[d]imidazol-2-yl)-2-methoxyaniline

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

The product from Step A (3.09 g, 9.14 mmol) was added to glacial acetic acid (250 mL). Zinc (21.68 g, 331.7 mmol) was gradually added with stirring. After stirring 1.5 hours, zinc was filtered from the mixture and the solution was concentrated to a dark oil. Methylene chloride (100 mL) was added to the oil and the desired product crystallized out overnight (0.3154 g), mp>300° C.

Workup

  1. stirringAfter stirring 1.5 hours
  2. filtrationzinc was filtered from the mixture
  3. concentrationthe solution was concentrated to a dark oil
  4. additionMethylene chloride (100 mL) was added to the oil
  5. customthe desired product crystallized out overnight (0.3154 g), mp>300° C.

Sources & evidence

ORD record
ord-a6ae282e52814d0490ec7cfe8ac9d3ba
Source dataset
uspto-grants-2005_02
Patent number
US06858739B2

Reaction notes

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