Toluene → Benzanilide

HRID 2304778Notes

Reaction equation

HRID 2304778 reaction equation
CCCCCC.C1(C)C=CC=CC=1.C([N:17]([C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)C=C.[OH-].[Na+]>ClC(Cl)C(P(C1C=CC=CC=1)C1C=CC=CC=1)(P(C1C=CC=CC=1)C1C=CC=CC=1)C.[Ni].C(OCC)C>[C:24]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:31])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 8058HexaneHCID 14798Sodium HydroxideHCID 14174668HCID 14174668, compound

Product 1

HCID 7168BenzanilideYield 73%

Reagents, catalysts & solvents 2

HCID 131723444HCID 131723444, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

Trimetyl alminum (0.98M n-hexane solution, 1.3 ml, 1.3 mmol) was added to an anhydrous toluene solution (2 ml) of N-allyl-N-benzoyl aniline (100 mg, 422 mmol) and nickel dichloro bis (diphenyl phosphino) propane (9 mg, 17 mmol) under ice cooling, and the mixture was refluxed for 7 hours. After the reaction, diethyl ether (3 ml) and a 0.5N solution (1.3 ml) of sodium hydroxide were added under ice cooling, and the mixture was stirred at room temperature for 2 hours. The reaction solution was dried over anhydrous magnesium sulfate, cerite was added thereto, the mixture was filtered, and the solvent was distilled away from the filtrate in vacuo. The resulting residue was subjected to silica gel chromatography (elution solution: diethyl ether/n-hexane=1/5, v/v) to N-benzoyl aniline (61 mg, yield 73%).

Workup

  1. temperaturethe mixture was refluxed for 7 hours
  2. dry with materialThe reaction solution was dried over anhydrous magnesium sulfate, cerite
  3. additionwas added
  4. filtrationthe mixture was filtered
  5. distillationthe solvent was distilled away from the filtrate in vacuo
  6. washelution solution

Sources & evidence

ORD record
ord-6c893c3b3a5a4deb9c753b0cb72fa2cf
Source dataset
uspto-grants-2002_08
Patent number
US06437133B1

Reaction notes

Loading…