2-Chloro-3-nitropyridine → 2-[(3-Nitropyridin-2-yl)sulfanyl]pyrimidine

HRID 1654616Notes

Reaction equation

HRID 1654616 reaction equation
[SH:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1>[OH-].[Na+].CS(C)=O>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[S:1][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 2

HCID 796132-Chloro-3-nitropyridineHCID 178418793HCID 178418793, compound

Product 1

HCID 1003182-[(3-Nitropyridin-2-yl)sulfanyl]pyrimidineYield 74%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
82 °C

Procedure

A mixture of 2.8 g of 2-mercaptopyrimidine in 35 ml 5.5% aqueous sodium hydroxide solution was added to 3.95 g 2-chloro-3-nitropyridine in 15 ml DMSO that was preheated to 92° C. The mixture, already containing precipitated product, cooled, and then was reheated to reflux at 82° C. After one hour, the reaction was allowed to cool and then poured into 150 ml ice-water. The precipitate was collected by filtration, washed with water and 95% ethanol, and then recrystallized from 95% ethanol to give 4.34 g (74% yield), mp 122.5°-124° C.

Workup

  1. customwas preheated to 92° C
  2. additionThe mixture, already containing
  3. customprecipitated product
  4. temperaturecooled
  5. temperatureto cool
  6. additionpoured into 150 ml ice-water
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with water and 95% ethanol
  9. customrecrystallized from 95% ethanol
  10. customto give 4.34 g (74% yield), mp 122.5°-124° C.

Sources & evidence

ORD record
ord-28184099423b462ab24d529943911cea
Source dataset
uspto-grants-1995_04
Patent number
US05409809

Reaction notes

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