Chloroform → 1-Hexadecyloxy-3-(4-bromobutylaminocarbonyloxy)-2-methylenepropane

HRID 2166432Notes

Reaction equation

HRID 2166432 reaction equation
[CH2:1]([O:17][CH2:18][C:19](=[CH2:22])[CH2:20][OH: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].[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]=[C:29]=[O:30].C(Cl)(Cl)Cl>CCOCC.CN(C)C1C=CN=CC=1>[CH2:1]([O:17][CH2:18][C:19](=[CH2:22])[CH2:20][O:21][C:29]([NH:28][CH2:27][CH2:26][CH2:25][CH2:24][Br:23])=[O:30])[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

6

Reactant 3

HCID 6212ChloroformHCID 113588863-Hexadecyloxy-2-methylenepropan-1-olHCID 149715841-Bromo-4-isocyanatobutane

Product 1

HCID 230396051-Hexadecyloxy-3-(4-bromobutylaminocarbonyloxy)-2-methylenepropane

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
22 °C

Procedure

3-Hexadecyloxy-2-methylenepropane-1-ol (from Preparation 1) (2.0 g) was dissolved in ether (40 ml). 4-Dimethylaminopyridine (0.16 g) and 4-bromobutyl isocyanate (1.6 g) were added, and the mixture was stirred for 22 hours at 22° C. Chloroform (40 ml) was added, and the mixture was purified through a column of silica gel 60 (70-230 mesh, 20 g) eluting with ether/chloroform 1:1. Further purification was achieved by chromatography on a Waters PrepLC®/System 500A using a prepPAK®-500/SILICA cartridge with ether/chloroform 1:1 as eluent.

Workup

  1. customthe mixture was purified through a column of silica gel 60 (70-230 mesh, 20 g)
  2. washeluting with ether/chloroform 1:1
  3. customFurther purification

Sources & evidence

ORD record
ord-26857d8351d94a44b3a9628a154e44c4
Source dataset
uspto-grants-1990_07
Patent number
US04945098

Reaction notes

Loading…