2-(Dimethylamino)ethanol → (+/-)-3-hexadecylthio-2-ethoxy-N,N-dimethyl-N-beta-hydroxyethyl-1-propyl ammonium bromide

HRID 977288Notes

Reaction equation

HRID 977288 reaction equation
[Br-].[CH2:2]([S:18][CH2:19][CH:20]([O:28][CH3:29])[CH2:21][N+:22]([CH3:27])([CH3:26])[CH2:23][CH2:24][OH:25])[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][CH2:16][CH3:17].[CH2:30](SCC(OCC)C[Br:50])CCCCCCCCCCCCCCC.CN(CCO)C>>[Br-:50].[CH2:2]([S:18][CH2:19][CH:20]([O:28][CH2:29][CH3:30])[CH2:21][N+:22]([CH3:26])([CH3:27])[CH2:23][CH2:24][OH:25])[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][CH2:16][CH3:17]

Participants

4

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 451658(3-Hexadecylsulfanyl-2-methoxy-propyl)-(2-hydroxyethyl)-dimethyl-ammoniumHCID 14522782(+/-)-1-Hexadecylthio-2-ethoxy-3-bromopropane

Product 1

HCID 14522784(+/-)-3-hexadecylthio-2-ethoxy-N,N-dimethyl-N-beta-hydroxyethyl-1-propyl ammonium bromideYield 30%

Procedure

This product was prepared in an analogous manner to that of (±)-3-hexadecylthio-2-methoxy-N, N-dimethyl-N-β-hydroxyethyl-1-propyl ammonium bromide from 2.2 grams (0.005 mole) of (±)-1-hexadecylthio-2-ethoxy-3-bromopropane and 0.15 milliliter (0.006 mole) of N,N-dimethylaminoethanol to give 0.775 milligram (30%) of product, (mp 112°-113° Centigrade). 1H-NMR (CDCl3): delta, 0.87(t, 3H, terminal methyl), 1.2-1.6[m, 31H, (CH2)14, CH3 --CH2 --O], 2.58(m, 2H, S--CH2), 2.7-2.9(m, 2H, CH2 --S), 3.48[s, 6H, N(CH3)2 ], 3.9-4.3(m, 9H, CH, CH2 --N--CH2 --CH2 --OH, CH3 --CH2 --O). Anal. (C25H54NO2SBr) C,H,N.

Sources & evidence

ORD record
ord-55784792b06f41198cc85b1e7a68b1db
Source dataset
uspto-grants-1997_03
Patent number
US05614548

Reaction notes

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