1-Chloro-2-(diethylamine)ethane hydrochloride → HCID 22327404, compound

HRID 495652Notes

Reaction equation

HRID 495652 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2[C:14]([C:20]([F:23])([F:22])[F:21])=[CH:15][C:16]([C:18]#[N:19])=[CH:17][C:12]=2[NH:11][C:10]1=[O:24].[H-].[Na+].[CH3:27][CH2:28][N:29]([CH2:32][CH2:33]Cl)[CH2:30][CH3:31].Cl.[C:36](=[O:39])(O)[O-:37].[Na+]>CN(C)C=O.C(N(CC)CC)C>[F:21][C:20]([F:23])([F:22])[C:36]([OH:37])=[O:39].[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2[C:14]([C:20]([F:23])([F:21])[F:22])=[CH:15][C:16]([C:18]([NH2:19])=[O:37])=[CH:17][C:12]=2[N:11]([CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[C:10]1=[O:24]

Participants

7

Reactant 4

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 22327357HCID 22327357, compound

Product 1

HCID 22327404HCID 22327404, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

1-(2,4-Dichlorophenyl)-2-oxo-7-(trifluoromethyl)-2,3-dihydro-1H-benzimidazole-5-carbonitrile (0.1541 g) was dissolved in N,N-dimethylformamide (5 ml), and to the solution was added sodium hydride (21.5 mg). The mixture was stirred at room temperature for 5 minutes. To the mixture were added 2-chlorotriethylamine hydrochloride (92.6 mg) and triethylamine (0.087 ml), and the mixture was stirred at 60-70° C. for 15 hours. After allowing to cool, to the reaction mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resultant residue was dissolved in 2-methyl-2-propanol (10 ml) and heated at 50° C. To the solution was added powdered potassium hydroxide (0.5810 g), and the mixture was stirred for 1 hour. After allowing to cool, to the reaction mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resultant residue was purified by HPLC using condition 1 to give the title compound (88.3 mg, 35%).

Workup

  1. stirringthe mixture was stirred at 60-70° C. for 15 hours
  2. temperatureto cool, to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. dissolutionThe resultant residue was dissolved in 2-methyl-2-propanol (10 ml)
  8. temperatureheated at 50° C
  9. additionTo the solution was added powdered potassium hydroxide (0.5810 g)
  10. stirringthe mixture was stirred for 1 hour
  11. temperatureto cool, to the reaction mixture
  12. additionwas added saturated aqueous sodium bicarbonate solution
  13. extractionthe mixture was extracted with ethyl acetate
  14. washThe organic layer was washed with saturated brine
  15. dry with materialdried over anhydrous sodium sulfate
  16. concentrationconcentrated in vacuo
  17. customThe resultant residue was purified by HPLC

Sources & evidence

ORD record
ord-1601e5b7bde64da4ae5a3218bf094d30
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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