Iodoethane → 1-Ethyl-2-[[[4-(tetradecyloxy)benzoyl]amino]methyl]pyridinium iodide

HRID 1728796Notes

Reaction equation

HRID 1728796 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9](=[O:31])[C:10]1[CH:15]=[CH:14][C:13]([O: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][CH3:30])=[CH:12][CH:11]=1.[CH2:32]([I:34])[CH3:33]>>[I-:34].[CH2:32]([N+:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9](=[O:31])[C:10]1[CH:11]=[CH:12][C:13]([O: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][CH3:30])=[CH:14][CH:15]=1)[CH3:33]

Participants

3

Reactant 2

HCID 6340IodoethaneHCID 10093859N-(2-Pyridinylmethyl)-4-(tetradecyloxy)benzamide

Product 1

HCID 190162261-Ethyl-2-[[[4-(tetradecyloxy)benzoyl]amino]methyl]pyridinium iodide

Conditions

Temperature
140 °C

Procedure

A mixture of 1.0 g of product from Example 4 and 9.42 ml of ethyl iodide is heated, in a sealed dark tube, at 140° C. for 20 hours. The cooled reaction mixture is concentrated in vacuo, the residue purified by column chromatography (silica gel:10% methyl alcohol/chloroform) and recrystallized from 5% chloroform/methyl alcohol to give 0.96 g of the desired product.

Workup

  1. customThe cooled reaction mixture
  2. concentrationis concentrated in vacuo
  3. customthe residue purified by column chromatography (silica gel:10% methyl alcohol/chloroform)
  4. customrecrystallized from 5% chloroform/methyl alcohol

Sources & evidence

ORD record
ord-acee8b7285e34c37a3f4c12f8a2d4253
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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