Acetonitrile → 1-Ethyl-N-methyl-N-pyridin-2-yl-1H-benzimidazol-2-amine

HRID 2113385Notes

Reaction equation

HRID 2113385 reaction equation
N1C=CC=C[C:2]=1[CH2:7][NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[C:16](#[N:18])[CH3:17].[CH2:19]([N:21](CC)[CH2:22]C)C.C[C:27]([CH3:32])([CH3:31])C(Cl)=O>O>[CH2:7]([N:8]1[C:9]2[CH:10]=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]=[C:19]1[N:21]([CH3:22])[C:32]1[CH:27]=[CH:31][CH:17]=[CH:16][N:18]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 73759Bis(2-pyridylmethyl)amine

Product 1

HCID 666282671-Ethyl-N-methyl-N-pyridin-2-yl-1H-benzimidazol-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask were added 1.06 g of di-(2-picolyl)amine and 20 ml of acetonitrile. The solution was stirred under nitrogen, when 0.7 g of triethylamine were added, followed by 1.5 g of trimethylacetyl chloride. After 1 hour, 20 ml of water were added and the acetonitrile was removed. The product was extracted with ethyl acetate and washed with water. Following solvent removal, the product was recrystallized by dissolving in 6 ml hot hexane with 0.5 ml 2-propanol. Another 2 ml hexane were added and the mixture was cooled to 5 C, filtered, washed with hexane and dried, resulting in 1.3 g of an off-white solid.

Workup

  1. customthe acetonitrile was removed
  2. extractionThe product was extracted with ethyl acetate
  3. washwashed with water
  4. customFollowing solvent removal
  5. customthe product was recrystallized
  6. dissolutionby dissolving in 6 ml hot hexane with 0.5 ml 2-propanol
  7. additionAnother 2 ml hexane were added
  8. temperaturethe mixture was cooled to 5 C
  9. filtrationfiltered
  10. washwashed with hexane
  11. customdried

Sources & evidence

ORD record
ord-77e8045bcfe8450a9977152da9d76c2c
Source dataset
uspto-grants-2009_04
Patent number
US07525717B2

Reaction notes

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