Benzoyl chloride → HCID 10363817, compound

HRID 1720910Notes

Reaction equation

HRID 1720910 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8](=[N:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[NH:9][C:10]#[N:11])[CH:5]=[N:6][CH:7]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C=O)C>[C:29]([NH:1][C:2]1[CH:3]=[C:4]([C:8](=[N:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[NH:9][C:10]#[N:11])[CH:5]=[N:6][CH:7]=1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 9817785HCID 9817785, compound

Product 1

HCID 10363817HCID 10363817, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-amino-N-cyano-N'-[2-(2-chlorophenyl)ethyl]-3-pyridinecarboximidamide (100 mg, 0.33 mmol) in DMF (3 ml) were added triethylamine (101 mg, 1 mmol) and benzoyl chloride (94 mg, 0.67 mmol), and the mixture was stirred at room temperature for 3 hours. After the reaction was completed, the reaction mixture was neutralized by adding ice and a saturated aqueous sodium carbonate solution and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (Wako Gel C-200, 30 g; eluted with chloroform:methanol=200:1) to give the title compound (38 mg, 0.09 mmol, yield 29%).

Workup

  1. additionby adding ice
  2. extractiona saturated aqueous sodium carbonate solution and extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography (Wako Gel C-200, 30 g; eluted with chloroform:methanol=200:1)

Sources & evidence

ORD record
ord-1ef9d46208574653ad47c994508524b3
Source dataset
uspto-grants-1996_04
Patent number
US05508293

Reaction notes

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