Sodium hydride → HCID 14769998, compound

HRID 477051Notes

Reaction equation

HRID 477051 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20]>C(O)C.O1CCOCC1>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([S:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)=[C:12]([N+:19]([O-:21])=[O:20])[CH:13]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 251404-Chloro-3-nitroanisoleHCID 178418431pyridine-4-thiol

Product 1

HCID 14769998HCID 14769998, compoundYield 21.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

1.11 g of 4-mercaptopyridine was dissolved in 5 ml of ethanol, and 52.8 mg of sodium hydride was added little by little. The mixture was stirred for 5 minutes, and then a solution of 1.87 g of 4-chloro-3-nitroanisole in 5 ml of dioxane was added. The mixture was heated under reflux at 100° C. for 15 hours. The solvent was evaporated, and 2N hydrochloric acid was added to the residue. The residue was washed with ether, made alkaline by adding an aqueous solution of sodium hydroxide, and extracted with methylene chloride. The extract was washed with a saturated aqueous solution of sodium chloride. The solvent was evaporated. The resulting residue was subjected to silica gel column chromatography. The column was eluted with a 5:3 mixture of hexane and acetone, and the eluate was recrystallized from acetone-hexane to give 562 mg (yield 21.4%) of 4-(4-methoxy-2-nitrophenyl)thiopyridine as orange needles having a melting point of 57° to 59° C.

Workup

  1. temperatureThe mixture was heated
  2. customThe solvent was evaporated
  3. addition2N hydrochloric acid was added to the residue
  4. washThe residue was washed with ether
  5. additionby adding an aqueous solution of sodium hydroxide
  6. extractionextracted with methylene chloride
  7. washThe extract was washed with a saturated aqueous solution of sodium chloride
  8. customThe solvent was evaporated
  9. washThe column was eluted with a 5:3 mixture of hexane and acetone
  10. customthe eluate was recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-abb458d1dfa640ffa1faeb8fa1ca9a7b
Source dataset
uspto-grants-1989_12
Patent number
US04886822

Reaction notes

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