2-Chloropyridine → 4-[(Pyridin-2-yl)sulfanyl]aniline
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([SH:15])=[CH:11][CH:10]=1.[OH-].[K+]>O1CCOCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[S:15][C:12]1[CH:13]=[CH:14][C:9]([NH2:8])=[CH:10][CH:11]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 22.7 g of 2-chloropyridine, 25 g of 4-aminothiophenol, 12.4 g of potassium hydroxide and 100 ml of dioxane was heated at 60° C. for about 2 hours to react them, and the product was purified to obtain 34.2 g of 4-(pyridine-2-ylthio) aniline. A mixture of 10 g of 4-(pyridine-2-ylthio) aniline, 5.6 g of triethylamine and 70 ml of chloroform was cooled at lower 5° C. in nitrogen gas atmosphere and 17 g of trifluoromethanesulfonic anhydride was added dropwise to the mixture. After the addition, the mixture was further stirred at 40° to 50° C. for about 1 hour to react them.
Workup
- customto react them
- customthe product was purified
Sources & evidence
- ORD record
- ord-d713263e6b26453f9cb2437888333c49
- Source dataset
- uspto-grants-1980_08
- Patent number
- US04218237
Reaction notes
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