p-Toluenesulfonic acid → HCID 18770656, compound

HRID 479525

Reaction equation

HRID 479525 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.C(O[CH:14](OCC)[CH2:15][CH3:16])C.[NH:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[N:21]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N:20]1([CH:14]([NH:8][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:15][CH3:16])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[N:21]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 120844-ChlorobenzamideHCID 20858Propane, 1,1-diethoxy-HCID 178418385HCID 178418385, compound

Product 1

HCID 18770656HCID 18770656, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 4-chlorobenzamide (1.50 g, 9.6 mmol), propionaldehyde diethyl acetal (1.53 g, 11.6 mmol), and benzotriazole (1.15 g, 9.6 mmol) in toluene (35 mL) was treated with p-toluenesulfonic acid (100 mg, 0.53 mmol). The mixture was heated at reflux under Dean-Stark conditions for 16 hours, cooled to ambient temperature, and concentrated to dryness. The crude material was purified by flash chromatography (elution with 40% ethyl acetate/hexanes) to provide 0.860 g of the desired product as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under Dean-Stark conditions for 16 hours
  3. concentrationconcentrated to dryness
  4. customThe crude material was purified by flash chromatography (elution with 40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-5baf35a8abbc4aef94eb3a9a7b85d8fb
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Linked notes

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