m-Chloroperbenzoic acid → HCID 178510664, compound

HRID 1285220Notes

Reaction equation

HRID 1285220 reaction equation
[C:1]([C:3]1[NH:7][CH:6]=[N:5][C:4]=1[NH:8][C:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)=[O:10])#[N:2].C(Cl)(=[O:24])C1C=CN=CC=1.FC1C=C(C=CC=1)C(Cl)=O.ClC1C=CC=C(C(OO)=O)C=1>C(OCC)(=O)C>[C:1]([C:3]1[NH:7][CH:6]=[N:5][C:4]=1[NH+:8]([O-:24])[C:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)=[O:10])#[N:2]

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 743763-Fluorobenzoyl chlorideHCID 417436Pyridine-4-carbonyl chlorideHCID 13588467N-(5-cyano-1H-imidazol-4-yl)-4-pyridinecarboxamide

Product 1

HCID 178510664HCID 178510664, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of N-(5-cyano-1H-imidazol-4-yl)-4-pyridinecarboxamide (0.53 g, 0.0025 mole), which can be made by the procedure of Example 1 substituting isonicotinoyl chloride for the 3-fluorobenzoyl chloride, in 20 ml of ethyl acetate was added 3-chloroperbenzoic acid (0.65 g, 0.003 mole). The mixture was heated at reflux for 15 hours, cooled and the solid product collected by filtration. The solid was washed with ethyl acetate and dried under reduced pressure to give N-(5-cyano-1H-imidazol-4-yl)-4-pyridinecarboxamide N-oxide (0.52 g; mp, 290°).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 15 hours
  3. temperaturecooled
  4. filtrationthe solid product collected by filtration
  5. washThe solid was washed with ethyl acetate
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-9a85c6bd15f84c62a47eddf82f890510
Source dataset
uspto-grants-1986_01
Patent number
US04565875

Reaction notes

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