Quinoline → 2-Methoxy-1-octadecylcarbamoylthio-3-(3-quinoliniopropylsulfonylamino)propane iodide

HRID 728434Notes

Reaction equation

HRID 728434 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][S:5]([NH:8][CH2:9][CH:10]([O:34][CH3:35])[CH2:11][S:12][C:13](=[O:33])[NH: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][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:7])=[O:6].C(Cl)(Cl)Cl.CO.[N:42]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:45]=[CH:44][CH:43]=1>>[I-:1].[CH3:35][O:34][CH:10]([CH2:9][NH:8][S:5]([CH2:4][CH2:3][CH2:2][N+:42]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:45]=[CH:44][CH:43]=1)(=[O:7])=[O:6])[CH2:11][S:12][C:13](=[O:33])[NH: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][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 3

HCID 7047QuinolineHCID 148350343-(3-Iodopropylsulfonylamino)-2-methoxy-1-octadecylcarbamoylthiopropaneHCID 21584188Chloroform methanol

Product 1

HCID 148348812-Methoxy-1-octadecylcarbamoylthio-3-(3-quinoliniopropylsulfonylamino)propane iodide

Procedure

A solution of 88 mg (0.136 mM) of 3-(3-iodopropylsulfonylamino)-2-methoxy-1-octadecylcarbamoylthiopropane IIa6 in 1 ml of quinoline is stirred at 45° C. for 2 days and the product is isolated by extraction with a mixture of chloroform-methanol and the organic layer is washed with 5.7% hydroiodic acid twice and with water once and the solvent is evaporated. The residue is recrystallized from acetone to give 2-methoxy-1-octadecylcarbamoylthio-3-(3-quinoliniopropylsulfonylamino)propane iodide Ia25.

Workup

  1. washthe organic layer is washed with 5.7% hydroiodic acid twice
  2. customwith water once and the solvent is evaporated
  3. customThe residue is recrystallized from acetone

Sources & evidence

ORD record
ord-fd293846fd2546d983a5e6de52b6daeb
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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