Water → 4-Isobutylthio-2-pyridyl methanesulfonate
Reaction equation
[CH2:1]([S:5][C:6]1[CH:11]=[CH:10][NH:9][C:8](=[O:12])[CH:7]=1)[CH:2]([CH3:4])[CH3:3].[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:13][S:14]([O:12][C:8]1[CH:7]=[C:6]([S:5][CH2:1][CH:2]([CH3:4])[CH3:3])[CH:11]=[CH:10][N:9]=1)(=[O:16])=[O:15]Participants
Procedure
1.3 g of 4-isobutylthio-2-pyridone (m.p. 119° to 120° C.) and 0.7 ml of methanesulfonyl chloride were dissolved in 10 ml of methylene chloride, and cooled below 10° C. 1.5 ml of triethylamine was added dropwise to the solution with stirring. By stirring at room temperature for 4 hours, the reaction was completed. The reaction solution was poured into 100 ml of water, followed by addition of 100 ml of methylene chloride for separation. The methylene chloride layer was washed with water and saturated aqueous solution of common salt, then distilled to remove the solvent. The obtained residue was purified by silica-gel column chromatography (developer: benzene and n-hexane) to obtain 1.7 g of the objective 4-isobutylthio-2-pyridyl methanesulfonate (yield: 91.6%) as a colourless oil, which were allowed to stand to crystallization.
Workup
- temperaturecooled below 10° C
- stirringBy stirring at room temperature for 4 hours
- washThe methylene chloride layer was washed with water and saturated aqueous solution of common salt
- distillationdistilled
- customto remove the solvent
- customThe obtained residue was purified by silica-gel column chromatography (developer: benzene and n-hexane)
Sources & evidence
- ORD record
- ord-549f75ad1da7459b91660251ef5877f6
- Source dataset
- uspto-grants-1988_12
- Patent number
- US04791127
Reaction notes
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