p-Toluenesulfonic acid → N-[1-(1H-1,2,3-benzotriazol-1-yl)-2,2-dimethyl-3-phenylpropyl]-4-chlorobenzamide

HRID 2299053Notes

Reaction equation

HRID 2299053 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11][C:12]([CH3:22])([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:13]=O.[NH:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=[N:24]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[N:23]1([CH:13]([NH:8][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:12]([CH3:22])([CH3:11])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=[N:24]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 120844-ChlorobenzamideHCID 70520Benzenepropanal, alpha,alpha-dimethyl-HCID 178418385HCID 178418385, compound

Product 1

HCID 18770575N-[1-(1H-1,2,3-benzotriazol-1-yl)-2,2-dimethyl-3-phenylpropyl]-4-chlorobenzamideYield 43.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of p-chlorobenzamide (3.02 g, 20.0 mmol), the product from Example 18A (3.24 g, 20.0 mmol), and benzotriazole (2.38 g, 20.0 mmol) in benzene (75 mL) was treated with p-toluenesulfonic acid (190 mg, 1.00 mmol). The solution was heated at reflux under Dean-Stark conditions for 10 hours, then cooled gradually to ambient temperature. The solvent was removed under vacuum and the residue was purified by flash chromatography (elution with 15% EtOAc/hexanes) to provide the title compound (3.63 g) as a white solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux under Dean-Stark conditions for 10 hours
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by flash chromatography (elution with 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-53075c5b7caa4a0eb55995a422b0e766
Source dataset
uspto-grants-2002_12
Patent number
US06495576B2

Reaction notes

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