Benzoyl chloride → HCID 68471395, compound

HRID 502993Notes

Reaction equation

HRID 502993 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])=[N:5][N:4]=[C:3]1[C:14]1([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(C(C)C)CC)(C)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])=[N:5][N:4]=[C:3]1[C:14]1([NH:19][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 68466643HCID 68466643, compound

Product 1

HCID 68471395HCID 68471395, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 516892Sodium BicarbonateSolvent

Procedure

1-[4-Methyl-5-(2-methylphenyl)-1,2,4-triazol-3-yl]cyclopentanamine (270 mg) was dissolved in chloroform (5 ml) and then diisopropylethylamine (1.7 ml) and benzoyl chloride (0.48 ml) were added thereto, followed by stirring at room temperature for 19 hours. The reaction solution was diluted with a saturated aqueous sodium bicarbonate solution, followed by extraction with chloroform (10 ml×2). The organic layer was dried over anhydrous sodium sulfate and filtered and then the solvent was removed by evaporation under reduced pressure. The resulting residue was purified by column chromatography (methanol:chloroform=1:19) and the resulting solid was dissolved in ethanol (1 ml) and then a 1M aqueous sodium hydroxide solution (2 ml) was added thereto, followed by stirring at room temperature for 6 days. The resulting solid was collected by filtration and washed with water to obtain 51 mg of N-{1-[4-methyl-5-(2-methylphenyl)-1,2,4-triazol-3-yl]cyclopentyl}benzamide (white solid).

Workup

  1. extractionfollowed by extraction with chloroform (10 ml×2)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed by evaporation under reduced pressure
  5. customThe resulting residue was purified by column chromatography (methanol:chloroform=1:19)
  6. dissolutionthe resulting solid was dissolved in ethanol (1 ml)
  7. additiona 1M aqueous sodium hydroxide solution (2 ml) was added
  8. stirringby stirring at room temperature for 6 days
  9. filtrationThe resulting solid was collected by filtration
  10. washwashed with water

Sources & evidence

ORD record
ord-3c6953f587404121aae04955250bd37f
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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