Pyridine → HCID 44548540, compound

HRID 1951596Notes

Reaction equation

HRID 1951596 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)[O:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.ClCCl.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.N1C=CC=CC=1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:23](=[O:30])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:15][CH:14]=3)[O:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 57465381HCID 57465381, compound

Product 1

HCID 44548540HCID 44548540, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

under an N2 atmosphere, 4-(4-(3-chlorophenyl)oxazol-2-yl)benzenamine (0.127 g, 0.469 mmol) was dissolved in dichloromethane (4.00 ml, 62.2 mmol). Benzoyl chloride (0.0572 ml, 0.493 mmol) was added followed by pyridine (0.200 ml, 2.47 mmol), and the reaction was allowed to stir at room temperature for 2.5 hours. The reaction was diluted with ethyl acetate and washed with 0.1N N HCl, and 5% NaHCO3. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude solid was triturated with ethyl acetate/hexanes and the resulting solid was collected by filtration to afford N-(4-(4-(3-chlorophenyl)oxazol-2-yl)phenyl)benzamide (0.112 g, 63.7% yield). ESI m/z=375.1 (M+H+).

Workup

  1. washwashed with 0.1N N HCl, and 5% NaHCO3
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude solid was triturated with ethyl acetate/hexanes
  6. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-21cf3dd239184f0f803f08241078de98
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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