Sodium hydride → HCID 22481986, compound

HRID 2182146Notes

Reaction equation

HRID 2182146 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[H-].[Na+].[Cl:12][C:13]1[CH:18]=[N:17][CH:16]=[C:15](Cl)[N:14]=1>C1(C)C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[N:17][CH:16]=[C:15]([O:6][CH2:5][C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[CH:3]=2)[N:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 701173-Chlorobenzyl alcoholHCID 785042,6-Dichloropyrazine

Product 1

HCID 22481986HCID 22481986, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-chlorobenyl alcohol (9.57 g, 67.1 mmol) in toluene (134 ml) at 23° C. under a nitrogen atmosphere was treated with NaH (60% dispersion in oil, 2.5 g, 67.1 mmol). The resulting suspension was heated to reflux for 30 min and cooled to room temperature. The mixture was treated with 2,6-dichloropyrazine (10.0 g, 67.1 mmol) and heated to reflux for 18 h. The reaction mixture was cooled to room temperature and partitioned between water and EtOAc. The organic phase was washed with brine, dried over MgSO4 (anhydrous), filtered and concentrated in vacuo. The residue was purified by flash chromatography (CH2Cl2-hexanes 3:7) to afford 10.0 g of the title compound (I-3l) as a clear oil (58%).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for 30 min
  3. temperatureheated
  4. temperatureto reflux for 18 h
  5. temperatureThe reaction mixture was cooled to room temperature
  6. custompartitioned between water and EtOAc
  7. washThe organic phase was washed with brine
  8. dry with materialdried over MgSO4 (anhydrous)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash chromatography (CH2Cl2-hexanes 3:7)

Sources & evidence

ORD record
ord-669b0bc8a442406d9d092d78fa7c17d7
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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