Dimethylformamide → (3-Hexadecylsulfanyl-2-methoxy-propyl)-(2-hydroxyethyl)-dimethyl-ammonium
Reaction equation
[CH2:1]([S:17][CH2:18][CH:19]([O:22][CH3:23])[CH2:20][Br:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:24][N:25]([CH2:27][CH2:28][OH:29])[CH3:26].CN(C=O)C>CCOCC>[Br-:21].[CH2:1]([S:17][CH2:18][CH:19]([O:22][CH3:23])[CH2:20][N+:25]([CH3:26])([CH3:24])[CH2:27][CH2:28][OH:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]Participants
Procedure
Into a two neck 25 ml round bottom flask equipped with an air condenser, thermometer and stir bar, was placed 2.0 g (0.005 mol) of (+)-1-hexadecylthio-2-methoxy-3-bromopropane, 0.5 ml (0.006 mol) of N,N-dimethylaminoethanol and 15 ml of DMF. The solution was maintained at 45°-50° C. for 72 hours with continuous stirring. The reaction mixture was then cooled to room temperature, 125 ml of ether was added and the solution was kept at 0° C. for 24 hours. The resulting precipitate (800 mg) was filtered and swirled with five 50 ml portions ofetherto give (±)-3-hexadecylthio-2-methoxy-N,N-dimethyl-N-β-hydroxyethyl-1 -propyl ammonium bromide (32%), (mp 107°-109° C.). 1 H-NMR (CDCl3): delta, 0.87 (t, 3 H, terminal methyl), 1.2-1.6[m, 28 H, (CH2)14 ],2.45-3.0(m, 4 H, S-C2, CH2 -S), 3.48[s, 9 H, CH3 -O, N(CH3)2 ], 3.9-4.3(m, 7 H, CH, CH2N, N-CH2 -CH2 -OH). Anal. (C24H52NO2SBr) C,H,N.
Workup
- customInto a two neck 25 ml round bottom flask equipped with an air condenser
- temperatureThe solution was maintained at 45°-50° C. for 72 hours with continuous stirring
- filtrationThe resulting precipitate (800 mg) was filtered
Sources & evidence
- ORD record
- ord-7a89f887482d4349a61e58be03189119
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05770584
Reaction notes
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