Benzeneacetamide → HCID 44139723, compound

HRID 1294700Notes

Reaction equation

HRID 1294700 reaction equation
[C:1]1([CH2:7][C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][C:12]([CH3:16])([CH3:15])[CH:13]=O.[NH:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[N:18]1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[N:17]1([CH:13]([NH:10][C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:12]([CH3:16])([CH3:15])[CH3:11])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[N:18]1

Participants

6

Reactant 3

HCID 7680BenzeneacetamideHCID 12417PivalaldehydeHCID 178418385HCID 178418385, compound

Product 1

HCID 44139723HCID 44139723, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A suspension of phenylacetamide (2.9 g, 21.45 mmol), trimethylacetaldehyde (5.42 g, 63.00 mmol), and 1H-1,2,3-benzotriazole (2.56 g, 21.45 mmol) in toluene (75 mL) was treated with p-toluenesulfonic acid (0.200 g, 1.00 mmol). The solution was heated at reflux under Dean-Stark conditions for 10 hours, cooled gradually to ambient temperature. The mixture was concentrated under reduced pressure and purified by flash chromatography on silica gel (sequential elution with 10, 15, and 20% of ethyl acetate in methylene chloride) to provide 6.05 g of the title compound. MS (ESI+) m/z 323 (M+H)+.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux under Dean-Stark conditions for 10 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. custompurified by flash chromatography on silica gel (sequential elution with 10, 15, and 20% of ethyl acetate in methylene chloride)

Sources & evidence

ORD record
ord-66024c9be4e44403a472cfbd24e32070
Source dataset
uspto-grants-2007_07
Patent number
US07241776B2

Reaction notes

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