m-Chloroperbenzoic acid → 3-(1-(cyclohexyl(methyl)carbamoyl)-1H-imidazol-4-yl)pyridine 1-oxide

HRID 530301Notes

Reaction equation

HRID 530301 reaction equation
[CH:1]1([N:7]([CH3:21])[C:8]([N:10]2[CH:14]=[C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[N:12]=[CH:11]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:27]>C(Cl)(Cl)Cl>[CH:1]1([N:7]([CH3:21])[C:8]([N:10]2[CH:14]=[C:13]([C:15]3[CH:16]=[N+:17]([O-:27])[CH:18]=[CH:19][CH:20]=3)[N:12]=[CH:11]2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66554294N-cyclohexyl-N-methyl-4-(pyridin-3-yl)-1H-imidazole-1-carboxamide

Product 1

HCID 468314763-(1-(cyclohexyl(methyl)carbamoyl)-1H-imidazol-4-yl)pyridine 1-oxideYield 48.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of N-cyclohexyl-N-methyl-4-(pyridin-3-yl)-1H-imidazole-1-carboxamide (90 mg, 0.317 mmol) in chloroform (5 mL) was added 3-chlorobenzoperoxoic acid (149 mg, 0.475 mmol) in one portion. The reaction was allowed to stir at room temperature for 20 h. TLC showed the reaction to be complete and the mixture was evaporated to dryness. The residue was triturated with ether and the resulting white crystals were filtered off and dried in air. Recrystallisation from hot isopropanol gave a white powder (46 mg, 46%).

Workup

  1. customthe reaction
  2. customthe mixture was evaporated to dryness
  3. customThe residue was triturated with ether
  4. filtrationthe resulting white crystals were filtered off
  5. customdried in air
  6. customRecrystallisation from hot isopropanol

Sources & evidence

ORD record
ord-018791ce68784746babe848db5645b65
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

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