HCID 22285184, compound → HCID 22285174, compound

HRID 1061555Notes

Reaction equation

HRID 1061555 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([NH:18][C:19](=O)[CH3:20])[CH:10]=2)=[CH:5][CH:4]=1>[Fe].C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]3[N:15]=[C:19]([CH3:20])[NH:18][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 22285184HCID 22285184, compound

Product 1

HCID 22285174HCID 22285174, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-(4′-methoxy-4-nitrobiphenyl-3-yl)acetamide (500 mg), acetic acid (6 ml) and iron powder (308 mg) was stirred at 100° C. for 50 minutes, and then cooled to room temperature, and insoluble matter was removed by filtration using celite. A saturated sodium carbonate aqueous solution was added to the filtrate to render the liquid about pH 7, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 5-(4′-methoxyphenyl)-2-methylbenzimidazole (320 mg).

Workup

  1. temperaturecooled to room temperature
  2. custominsoluble matter was removed by filtration
  3. additionA saturated sodium carbonate aqueous solution was added to the filtrate
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-adabd54fe3624028939cdedbbe91cb98
Source dataset
uspto-grants-2005_11
Patent number
US06960591B2

Reaction notes

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