Water → 2-[acetyl(phenyl)amino]-N-[4-(4-pyridinyl)phenyl]acetamide

HRID 1510246Notes

Reaction equation

HRID 1510246 reaction equation
[NH:1]([CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32].O>CN(C)C=O>[C:31]([N:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1)=[O:10])(=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 159813822-anilino-N-[4-(4-pyridinyl)phenyl]acetamide

Product 1

HCID 576639652-[acetyl(phenyl)amino]-N-[4-(4-pyridinyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-anilino-N-[4-(4-pyridinyl)phenyl]acetamide (50 mg) in N,N-dimethylformamide (1.0 mL) were added triethylamine (0.092 mL) and acetyl chloride (0.0352 mL) at ambient temperature and the mixture was stirred at ambient temperature overnight. Water (3 mL) was added to the mixture and the resulting mixture was extracted with ethyl acetate (5 mL). The organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by preparative thin-layer chromatography (10% methanol in chloroform) to afford 2-[acetyl(phenyl)amino]-N-[4-(4-pyridinyl)phenyl]acetamide (46.9 mg) as a white amorphous.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (5 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by preparative thin-layer chromatography (10% methanol in chloroform)

Sources & evidence

ORD record
ord-59f3b7b289d3400b9f315e823741edbf
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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