2,6-Dichloropyridine → N-{4-[(6-Chloropyridin-2-yl)sulfanyl]phenyl}acetamide

HRID 1415087Notes

Reaction equation

HRID 1415087 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C[O-].[Na+].C(NC1C=CC(S)=CC=1)(=O)C.[Na].[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30](Cl)[N:29]=1>CS(C)=O>[Cl:27][C:28]1[N:29]=[C:30]([S:11][C:8]2[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=2)[CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 169892,6-DichloropyridineHCID 707774'-MercaptoacetanilideHCID 10942334Sodium MethoxideHCID 70634381HCID 70634381, compound

Product 1

HCID 21391453N-{4-[(6-Chloropyridin-2-yl)sulfanyl]phenyl}acetamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

4-Acetamidothiophenol (16.8 grams; 0.1 mole) was mixed with a solution of sodium methylate (prepared by mixing sodium metal (2.3 grams; 0.1 mole) in 90 ml. of methanol) and the resulting sodium 4-acetamidothiophenol solution added over a period of about one hour to a well-stirred solution of 2,6-dichloropyridine (14.8 grams; 0.1 mole) in 100 ml. of dimethylsulfoxide. The reaction mixture was distilled during the addition and the reaction temperature maintained at about 100° C. for this period and for a period of about 2 hours thereafter. The reaction mixture was then poured into 350 ml. of water and the resulting product precipitate recovered by filtration, washed several times and taken up in 300 ml. of hot benzene and dried and treated with Norite. About 350 ml. of hexane was added to precipitate the product from the bezene solvent which was recovered by filtration. As a result of such operations, the desired N-(4-((6-chloro-2-pyridinyl)thio)phenyl)acetamide compound was recovered as a crystalline solid which was found to have carbon, hydrogen, nitrogen, chlorine and sulfur contents of 56.2, 4.3, 9.9, 11.4 and 11.63 percent, respectively, as compared with the theoretical contents of 56.0, 3.96, 10.05, 12.7 and 11.45, respectively, calculated for the named structure.

Workup

  1. distillationThe reaction mixture was distilled during the addition
  2. additionThe reaction mixture was then poured into 350 ml
  3. filtrationof water and the resulting product precipitate recovered by filtration
  4. washwashed several times
  5. dry with materialof hot benzene and dried
  6. additiontreated with Norite
  7. additionof hexane was added
  8. customto precipitate the product from the bezene solvent which
  9. filtrationwas recovered by filtration
  10. customAs a result of such operations
  11. customthe desired N-(4-((6-chloro-2-pyridinyl)thio)phenyl)acetamide compound was recovered as a crystalline solid which

Sources & evidence

ORD record
ord-387fbf6f09f64caabe86d639abb7c327
Source dataset
uspto-grants-1977_01
Patent number
US04003734

Reaction notes

Loading…