Sodium Sulfide → 4-[(3-Chloropyrazin-2-yl)thio]-3-nitrobenzyl alcohol

HRID 1059292Notes

Reaction equation

HRID 1059292 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[S-2:13].[Na+].[Na+].[Cl:16][C:17]1[C:22](Cl)=[N:21][CH:20]=[CH:19][N:18]=1>CS(C)=O>[Cl:16][C:17]1[C:22]([S:13][C:2]2[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])=[N:21][CH:20]=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 14804Sodium SulfideHCID 785752,3-DichloropyrazineHCID 919334-Chloro-3-nitrobenzyl alcohol

Product 1

HCID 114379644-[(3-Chloropyrazin-2-yl)thio]-3-nitrobenzyl alcoholYield 67.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.876 g of 4-chloro-3-nitrobenzyl alcohol was dissolved in 20 ml of dimethyl sulfoxide. After adding 820 mg of anhydrous sodium sulfide, the resulting mixture was stirred at room temperature for 15 hours. After adding 1.19 g of 2,3-dichloropyrazine thereto, the reaction mixture was stirred at 100° C. for 1 hour. After adding ice/water, the reaction mixture was extracted with ethyl acetate, washed successively with water, 1 N hydrochloric acid, water, 1 N sodium hydroxide, and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane) to thereby give 1.60 g of the title compound as yellow crystals.

Workup

  1. stirringthe reaction mixture was stirred at 100° C. for 1 hour
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washwashed successively with water, 1 N hydrochloric acid, water, 1 N sodium hydroxide
  4. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-1fa8b70256df4fed95fdc8f02f027792
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

Loading…