Methyl iodide → 1-Methyl-2-[[(methylsulfonyl)[[4-(tetradecyloxy)phenyl]methyl]amino]methyl]pyridinium iodide

HRID 248024Notes

Reaction equation

HRID 248024 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:16][CH:15]=1)[S:9]([CH3:12])(=[O:11])=[O:10].[CH3:35][I:36]>>[I-:36].[CH3:35][N+:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]([S:9]([CH3:12])(=[O:11])=[O:10])[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 19014986N-(2-Pyridinylmethyl)-N-[[4-(tetradecyloxy)phenyl]methyl]methanesulfonamide

Product 1

HCID 190156101-Methyl-2-[[(methylsulfonyl)[[4-(tetradecyloxy)phenyl]methyl]amino]methyl]pyridinium iodideYield 99.6%

Conditions

Temperature
90 °C

Procedure

A mixture of 0.350 g of product from Example 122 and 5.08 g of methyl iodide is heated at 90° C. for 17 hours. Thin layer chromatography shows the presence of starting material. The mixture is reheated at 125° C. for 23 hours. The reaction is concentrated in vacuo to give 0.45 g of the desired product as pale yellow crystals.

Workup

  1. concentrationThe reaction is concentrated in vacuo

Sources & evidence

ORD record
ord-9f01f58637f44ec4a4c62a4f5ef6c238
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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