n-Methyl-p-aminophenol → 4-[N-methyl-N-(2-benzimidazolyl)amino]phenol

HRID 1446872

Reaction equation

HRID 1446872 reaction equation
Cl[C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1>C(#N)C.O>[CH3:11][N:12]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 5931n-Methyl-p-aminophenolHCID 785722-Chlorobenzimidazole

Product 1

HCID 133148184-[N-methyl-N-(2-benzimidazolyl)amino]phenolYield 58.7%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A mixture of 2-chlorobenzimidazole (1.0 g), 4-(N-methylamino)phenol (1.13 g) and acetonitrile/water (1:1) was heated under reflux for a period of 5 hours. The mixture was concentrated, made basic with dilute ammonium hydroxide and the solid was collected. The product was recrystallised from ethanol to give 4-[N-methyl-N-(2-benzimidazolyl)amino]phenol (0.92 g) as colourless crystals, mp>260° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for a period of 5 hours
  3. concentrationThe mixture was concentrated
  4. customthe solid was collected
  5. customThe product was recrystallised from ethanol

Sources & evidence

ORD record
ord-fac870d124ac453eb09f7b0f90d47b6a
Source dataset
uspto-grants-1982_02
Patent number
US04314065

Linked notes

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