Hydrochloric Acid → 3-[2-(diethylamino)ethyl]-2-oxo-7-(trifluoromethyl)-1-[3-(trifluoromethyl)benzyl]-2,3-dihydro-1H-benzimidazole-5-carbonitrile

HRID 495657Notes

Reaction equation

HRID 495657 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:5]2[C:18]([C:24]([F:27])([F:26])[F:25])=[CH:19][C:20]([C:22]#[N:23])=[CH:21][C:4]=2[NH:3]1.[H-].[Na+].[CH3:30][CH2:31][N:32]([CH2:35][CH2:36]Cl)[CH2:33][CH3:34].Cl.Cl.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(N(CC)CC)C>[CH2:31]([N:32]([CH2:35][CH3:36])[CH2:33][CH2:34][N:3]1[C:4]2[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[C:18]([C:24]([F:27])([F:25])[F:26])[C:5]=2[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:16])([F:17])[F:15])[CH:9]=2)[C:2]1=[O:1])[CH3:30]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 223273832-oxo-7-(trifluoromethyl)-1-[3-(trifluoromethyl)benzyl]-2,3-dihydro-1H-benzimidazole-5-carbonitrile

Product 1

HCID 223274103-[2-(diethylamino)ethyl]-2-oxo-7-(trifluoromethyl)-1-[3-(trifluoromethyl)benzyl]-2,3-dihydro-1H-benzimidazole-5-carbonitrileYield 103.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-oxo-7-(trifluoromethyl)-1-[3-(trifluoromethyl)benzyl]-2,3-dihydro-1H-benzimidazole-5-carbonitrile (139.5 mg) in N,N-dimethylformamide (5 ml) was added sodium hydride (60%) (38.0 mg). After the mixture was stirred at room temperature for 10 minutes, 2-chlorotriethylamine hydrochloride (89.4 mg) and triethylamine (0.120 ml) were added, and the mixture was stirred with heating at 70° C. for 1.5 hours. To the reaction mixture was added 1N hydrochloric acid, and the mixture was basified with saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (181 mg, quantitative yield).

Workup

  1. stirringthe mixture was stirred
  2. temperaturewith heating at 70° C. for 1.5 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3fac06bda5c04e32bc982c7c414c4da3
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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