Thionyl Chloride → HCID 13669337, compound
Reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH3:18])[CH:8]=1>ClCCl>[ClH:3].[Cl:3][CH2:6][C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH3:18])[CH:8]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of thionyl chloride (9.48 g.) in dichloromethane (800 ml.) was added during 4 hours to a refluxing suspension of finely ground 3-hydroxymethyl-1-methyl-4-quinolone (15.01 g.) in dichloromethane (200 ml.). The mixture was boiled under reflux for a further 1.5 hours, cooled to room temperature and filtered to give the novel compound 3-chloromethyl-1-methyl-4-quinolone hydrochloride m.p. 178°-181°. This compound (12.71 g.) was added to a stirred solution of sodium methanethiolate in methanol at 0° (116 ml. containing 0.109 mole NaSCH3) during 5 minutes. The resulting mixture was allowed to warm to room temperature and kept overnight. The mixture was cooled to 0° and water added to form a solution. The solution was neutralised to pH 7.0 with dilute hydrochloric acid and filtered. Methanol was distilled from the filtrate and the residue extracted with dichloromethane (3×50 ml.). The combined extracts were dried over anhydrous magnesium sulphate and evaporated to give a solid product. The product was purified by high pressure liquid chromatography over silica gel, eluting with isopropanol:dichloromethane 15:85 at a flow rate of 300 ml. per minute. The same solvent was used for applying the product to the silica gel. This procedure gave the novel 1-methyl-3-methylthiomethyl-4-quinolone m.p. 118°-120°.
Workup
- temperatureunder reflux for a further 1.5 hours
- filtrationfiltered
Sources & evidence
- ORD record
- ord-bc3e715a12934632bd10151160587133
- Source dataset
- uspto-grants-1984_04
- Patent number
- US04442109
Reaction notes
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