m-Chloroperbenzoic acid → 3-(4-phenylthiazol-2-yl)pyridine-N-oxide

HRID 1421952Notes

Reaction equation

HRID 1421952 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=2)[CH:2]=1.ClC1C=CC=C(C(OO)=[O:26])C=1>ClCCl>[C:12]1([C:10]2[N:11]=[C:7]([C:3]3[CH:2]=[N+:1]([O-:26])[CH:6]=[CH:5][CH:4]=3)[S:8][CH:9]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 7010154-Phenyl-2-(pyridin-3-yl)thiazole

Product 1

HCID 187071743-(4-phenylthiazol-2-yl)pyridine-N-oxideYield 28.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 50 ml of dichloromethane was dissolved 1 g of 2-(pyridin-3-yl)-4-phenylthiazole. Thereto was added 900 mg of m-chloroperbenzoic acid at room temperature. The mixture was stirred at the same temperature for 2 hours. The reaction mixture was washed with an aqueous sodium hydrogencarbonate solution and dried. The solvent was removed by distillation. The residue was recrystallized from ethyl acetate to obtain 306 mg of 3-(4-phenylthiazol-2-yl)pyridine-N-oxide as a brown powder.

Workup

  1. washThe reaction mixture was washed with an aqueous sodium hydrogencarbonate solution
  2. customdried
  3. customThe solvent was removed by distillation
  4. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4448ef66953b4ec2b36f4920854be5c4
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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