p-Toluenesulfonic acid → HCID 18770637, compound

HRID 479529Notes

Reaction equation

HRID 479529 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[CH:11]1([C:17]([CH3:21])([CH3:20])[CH:18]=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[NH:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[N:23]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N:22]1([CH:18]([NH:8][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:17]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)([CH3:21])[CH3:20])[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[N:23]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 120844-ChlorobenzamideHCID 1400235028523-30-0HCID 178418385HCID 178418385, compound

Product 1

HCID 18770637HCID 18770637, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of p-chlorobenzamide (5.31 g, 35.10 mmol), 2-cyclohexyl-2-methylpropanal (4.5 g, 35.10 mmol), and benzotriazole (4.18 g, 35.10 mmol) in toluene (100 mL) was treated with p-toluenesulfonic acid (334 mg, 1.76 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 reduced pressure and the residue was purified by flash chromatography (elution with 10% EtOAc/hexane) to provide 5.3 g of the desired product 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 reduced pressure
  4. customthe residue was purified by flash chromatography (elution with 10% EtOAc/hexane)

Sources & evidence

ORD record
ord-2c1f2ec450d94e5a8b7ba308a4040026
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

Loading…