m-Chloroperbenzoic acid → HCID 22481997, compound

HRID 2182147Notes

Reaction equation

HRID 2182147 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[N:7]=1.ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:25])[CH:5]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[N:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22481986HCID 22481986, compound

Product 1

HCID 22481997HCID 22481997, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 3-chloro-5-(3-chloro-benzyloxy)-pyrazine I-3l (500 mg, 1.97 mmol) in CHCl3 (10 ml) at 0° C. under a nitrogen atmosphere, was treated with 680 mg (3.94 mmol) m-chloroperbenzoic acid (mCPBA). The resulting mixture was allowed to warm to room temperature, stirred at 23° C. for 16 h, heated at reflux for 2 h and cooled to room temperature. The reaction mixture was treated with Ca(OH)2 (680 mg, 3.94 mmol), stirred at room temperature for 3 h and filtered. The solid was washed with CH2Cl2. The filtrate and washings were combined, dried over MgSO4 (anhydrous), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc-hexanes 4:6) to provide 465 mg of the title compound (I-3m) as a white solid (87%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. temperaturecooled to room temperature
  4. stirringstirred at room temperature for 3 h
  5. filtrationfiltered
  6. washThe solid was washed with CH2Cl2
  7. dry with materialdried over MgSO4 (anhydrous)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography (EtOAc-hexanes 4:6)

Sources & evidence

ORD record
ord-0a00bd049f1b40dc8f4f59356df87253
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

Loading…