O-Phenylenediamine → 1-(4-methoxybenzyl)-2-(4-methoxyphenyl)-1H-benzo(d)imidazole

HRID 338808

Reaction equation

HRID 338808 reaction equation
[NH4+].[Br-].[C:3]1([NH2:10])[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH2:9].[CH:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1>CO>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:9]2[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[N:10]=[C:11]2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 25514Ammonium BromideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 7461821-(4-methoxybenzyl)-2-(4-methoxyphenyl)-1H-benzo(d)imidazoleYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a methanol (5 mL) solvent in the presence of NH4Br (362.3 mg, 3.70 mmol), a solution including 1,2-phenylenediamine (100 mg, 0.92 mmol) and p-anisaldehyde (0.11 mL, 0.82 mmol) was stirred at room temperature for 6 hours, and methanol was evaporated therefrom. The residual was distributed between ethyl acetate and water. An organic layer was dried by using MgSO4, filtered, and evaporated. The residual was purified by silica gel column chromatography using hexane and ethyl acetate (3:1) to obtain a solid Compound 116.

Workup

  1. custommethanol was evaporated
  2. customAn organic layer was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residual was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-59ce6cf1b0b44e61891f939e3809619a
Source dataset
uspto-grants-2014_11
Patent number
US08889881B2

Linked notes

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