Ethanol → N-Methyl-1H-benzo[d]imidazol-2-amine

HRID 1038900Notes

Reaction equation

HRID 1038900 reaction equation
Cl[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[CH3:11][NH2:12].CCO>CC(C)=O>[CH3:11][NH:12][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 785722-Chlorobenzimidazole

Product 1

HCID 676520N-Methyl-1H-benzo[d]imidazol-2-amineYield 51.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
160 °C

Procedure

2-Chloro-1H-benzo[d]imidazole (20 g, 131.08 mmol) was charged to high pressure autoclave PV10832 (Hastelloy 450 ml) with methylamine (260 mL, 131.08 mmol) and sealed on its trolley and the resulting solution heated to 160° C. in high pressure blast cell 60 for 16 hours. The pressure in the autoclave reached 11 bar. The solvent was removed under reduced pressure to afford a brown oil. EtOH was added and the solvent again removed to afford a brown foam. The foam was dissolved in a minimum of hot acetone. This was then allowed to cool. The resultant solid was filtered affording N-methyl-1H-benzo[d]imidazol-2-amine (9.91 g, 51%); 1H NMR (400 MHz, DMSO-d6) 2.83 (3H, s), 6.87-7.00 (2H, m), 7.05-7.25 (2H, m), 7.49 (1H, s).

Workup

  1. customsealed on its trolley
  2. customThe solvent was removed under reduced pressure
  3. customto afford a brown oil
  4. customthe solvent again removed
  5. customto afford a brown foam
  6. temperatureto cool
  7. filtrationThe resultant solid was filtered

Sources & evidence

ORD record
ord-5c0be413ff594cd3bef580233e22be2c
Source dataset
uspto-grants-2013_10
Patent number
US08552004B2

Reaction notes

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