Thiazole → 1-Hexadecylthio-2-methoxy-3-(3-thiazoliopropylsulfonylamino)propane iodide

HRID 728422Notes

Reaction equation

HRID 728422 reaction equation
[CH2:1]([S:17][CH2:18][CH:19]([O:29][CH3:30])[CH2:20][NH:21][S:22]([CH2:25][CH2:26][CH2:27][I:28])(=[O:24])=[O:23])[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].[S:31]1[CH:35]=[CH:34][N:33]=[CH:32]1>>[I-:28].[CH2:1]([S:17][CH2:18][CH:19]([O:29][CH3:30])[CH2:20][NH:21][S:22]([CH2:25][CH2:26][CH2:27][C:32]1[S:31][CH:35]=[CH:34][NH+:33]=1)(=[O:24])=[O:23])[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

3

Reactant 2

HCID 9256ThiazoleHCID 148350231-Hexadecylthio-3-(3-iodopropylsulfonylamino)-2-methoxypropane

Product 1

HCID 679030061-Hexadecylthio-2-methoxy-3-(3-thiazoliopropylsulfonylamino)propane iodideYield 56%

Procedure

A solution of 600 mg (1.04 mM) of 1-hexadecylthio-3-(3-iodopropylsulfonylamino)-2-methoxypropane IIa2 in 5 ml of thiazole is stirred at 60° C. for 6 hours. After thiazole is evaporated, the residue is washed with ether and recrystallized from acetone to give 387 mg (0.584 mM) of 1-hexadecylthio-2-methoxy-3-(3-thiazoliopropylsulfonylamino)propane iodide Ia9 in 56% yield.

Workup

  1. customAfter thiazole is evaporated
  2. washthe residue is washed with ether
  3. customrecrystallized from acetone

Sources & evidence

ORD record
ord-67ab0bfd55244b41b514a88a82774260
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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