Thionyl Chloride → HCID 19002316, compound
Reaction equation
[CH2:1]([S:15][CH2:16][CH2:17][C:18]([OH:20])=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].S(Cl)([Cl:23])=O>>[CH2:1]([S:15][CH2:16][CH2:17][C:18]([Cl:23])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]Participants
Procedure
A mixture consisting of 3-(tetradecylthio)propionic acid (3.02 g) and thionyl chloride (20 ml) was stirred for 30 minutes at room temperature and then evaporated under a reduced pressure to obtain 3-(tetradecylthio)propionyl chloride. The thus obtained 3-(tetradecylthio)propionyl chloride was dissolved in toluene (5 ml) and added dropwise to a mixture consisting of 2,6-diisopropylaniline (1.77 g), triethylamine (2.1 ml) and toluene (20 ml), followed by 1 hour of stirring at room temperature. The reaction mixture was washed with 3% hydrochloric acid, 10% sodium hydroxide solution and saturated brine successively and then dried on anhydrous magnesium sulfate. After removing the solvent by distillation under a reduced pressure, the resulting residue was subjected to a silica gel column chromatography (developing solvent; ethyl acetate:hexane=1:5) and then to crystallization using isopropyl ether, thereby obtaining the title compound (2.55 g) in the form of colorless needle crystals.
Workup
- customevaporated under a reduced pressure
Sources & evidence
- ORD record
- ord-44e92933c23b4c3182f87e87132b616a
- Source dataset
- uspto-grants-1995_12
- Patent number
- US05475130
Reaction notes
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