Triethylamine → 2-(2,6-Dichlorophenyl)-3H-benzimidazole-5-carboxylic acid [2-(4-chlorophenyl)-1-methyl-2-oxoethyl]-amide

HRID 1514906Notes

Reaction equation

HRID 1514906 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[C:10]1[NH:11][C:12]2[CH:18]=[C:17]([C:19](Cl)=[O:20])[CH:16]=[CH:15][C:13]=2[N:14]=1.C([N:24]([CH2:27][CH3:28])CC)C.C([O:32][CH2:33][CH3:34])(=O)C>C1COCC1>[Cl:1][C:3]1[CH:8]=[CH:7][C:34]([C:33](=[O:32])[CH:27]([NH:24][C:19]([C:17]2[CH:16]=[CH:15][C:13]3[N:14]=[C:10]([C:4]4[C:3]([Cl:2])=[CH:8][CH:7]=[CH:6][C:5]=4[Cl:9])[NH:11][C:12]=3[CH:18]=2)=[O:20])[CH3:28])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 866328172-(2,6-dichlorophenyl)-3H-benzimidazole-5-carbonyl chloride hydrochloride

Product 1

HCID 669655372-(2,6-Dichlorophenyl)-3H-benzimidazole-5-carboxylic acid [2-(4-chlorophenyl)-1-methyl-2-oxoethyl]-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(4-chlorophenyl)-2-aminopropiophenone hydrochloride (365 mg, 1.66 mmol), 2-(2,6-dichlorophenyl)-3H-benzimidazole-5-carbonyl chloride hydrochloride (600 mg, 1.66 mmol) (from Example 1-13) and triethylamine (924 μL, 671 mg, 6.63 mmol) in THF (25 mL) was stirred at ambient temperature for 18 h. The solution was then poured into ethyl acetate and extracted with water and brine. The organic layer was dried, filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography using a gradient of 50-90% heptane/ethyl acetate to give 2-(2,6-dichlorophenyl)-3H-benzimidazole-5-carboxylic acid [2-(4-chlorophenyl)-1-methyl-2-oxoethyl]-amide. 1H-NMR (acetone-d6, 400 MHz): δ 8.57 (m, broad, 1H), 8.37 (m, 3H), 8.11 (m, broad, 1H), 7.83 (m, 5H), 5.92 (quintet, J=7.2 Hz, 1H), 1.75 (d, J=7.0 Hz, 3H). MS (ESI) m/z 473.9 (M+H).

Workup

  1. extractionextracted with water and brine
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-90065dde628948169b93512d3c393401
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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