Methyl iodide → 2-[[Acetyl[[[4-(tetradecyloxy)phenyl]methoxy]carbonyl]amino]methyl]-1-methylpyridinium iodide

HRID 248005Notes

Reaction equation

HRID 248005 reaction equation
[C:1]([N:4]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)[C:5](=[O:29])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O: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])=[CH:10][CH:9]=1)(=[O:3])[CH3:2].[CH3:37][I:38]>>[I-:38].[C:1]([N:4]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N+:32]=1[CH3:37])[C:5]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O: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])=[CH:12][CH:13]=1)=[O:29])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 9983311[4-(Tetradecyloxy)phenyl]methyl acetyl(2-pyridinylmethyl)carbamate

Product 1

HCID 103491502-[[Acetyl[[[4-(tetradecyloxy)phenyl]methoxy]carbonyl]amino]methyl]-1-methylpyridinium iodideYield 93.7%

Conditions

Temperature
100 °C

Procedure

A mixture of 1.37 g of product from Example 96 and 19.55 g of methyl iodide is heated in a sealed tube at 100° C. for 5 hours. The reaction is concentrated in vacuo and the residue recrystallized from methyl alcohol to give 1.65 g of the desired product.

Workup

  1. concentrationThe reaction is concentrated in vacuo
  2. customthe residue recrystallized from methyl alcohol

Sources & evidence

ORD record
ord-038f003302c643be86b1536f6955fe6d
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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