Sodium Iodide → 1-Hexadecylthio-3-(3-iodopropylsulfonylamino)-2-methoxypropane

HRID 728421Notes

Reaction equation

HRID 728421 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([NH:8][CH2:9][CH:10]([O:29][CH3:30])[CH2:11][S:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])(=[O:7])=[O:6].[I-:31].[Na+]>C(C(C)=O)C>[CH2:13]([S:12][CH2:11][CH:10]([O:29][CH3:30])[CH2:9][NH:8][S:5]([CH2:4][CH2:3][CH2:2][I:31])(=[O:7])=[O:6])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 14835022HCID 14835022, compound

Product 1

HCID 148350231-Hexadecylthio-3-(3-iodopropylsulfonylamino)-2-methoxypropaneYield 87%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 1.03 g (2.12 mM) of 3-(3-chloropropylsulfonylamino)-1-hexadecylthio-2-methoxypropane IIIa2 in 20 ml of methyl ethyl ketone is added 636 mg (4.24 mM) of sodium iodide and the mixture is refluxed or 3 hours with stirring. After the solvent is evaporated, the residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (4:1) mixture as an eluent to give 1.06 g (1.835 mM) of 1-hexadecylthio-3-(3-iodopropylsulfonylamino)-2-methoxypropane IIa2 as an oil in 87% yield.

Workup

  1. temperaturethe mixture is refluxed or 3 hours
  2. customAfter the solvent is evaporated
  3. customthe residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (4:1) mixture as an eluent

Sources & evidence

ORD record
ord-e016fd2a5f1441589a03102ee6a52880
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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