m-Chloroperbenzoic acid → HCID 21075863, compound

HRID 1374158Notes

Reaction equation

HRID 1374158 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=2[C:15]2[N:16]=[N:17][N:18]([CH3:20])[N:19]=2)[CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:26]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:26])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=2[C:15]2[N:16]=[N:17][N:18]([CH3:20])[N:19]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 21075865HCID 21075865, compound

Product 1

HCID 21075863HCID 21075863, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-chloro-5-[3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]pyridine (2.90 g, 9.98 mmol) and 3-chloroperoxybenzoic acid (2.238 g, 12.97 mmol) in 40 mL CH2Cl2 was stirred at room temperature overnight. Additional 3-chloroperoxybenzoic acid (861 mg, 4.99 mmol) was added in the morning to drive the reaction to completion. The solution was washed with 0.5 N NaOH and brine, dried over Na2SO4, filtered and concentrated under vacuum to provide 3-chloro-5-[3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]pyridine 1-oxide that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 306.13 for M+H+.

Workup

  1. customthe reaction to completion
  2. washThe solution was washed with 0.5 N NaOH and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b818cd9f54104506803eef583a70e81c
Source dataset
uspto-grants-2007_01
Patent number
US07163951B2

Reaction notes

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