Methyl iodide → 2,3-Dimethyl-1-[4-[[[4-(tetradecyloxy)phenyl]acetyl]amino]phenyl]-1H-imidazolium iodide

HRID 484608Notes

Reaction equation

HRID 484608 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:37])[CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:18][CH:17]=3)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.[CH3:38][I:39]>C1(C)C=CC=CC=1.CCOCC>[I-:39].[CH3:1][CH:2]1[N:6]([CH3:38])[CH:5]=[CH:4][NH+:3]1[C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:14](=[O:37])[CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:20][CH:21]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 15030162N-[4-(2-methyl-1H-imidazol-1-yl)phenyl]-4-(tetradecyloxy)benzeneacetamide

Product 1

HCID 677870672,3-Dimethyl-1-[4-[[[4-(tetradecyloxy)phenyl]acetyl]amino]phenyl]-1H-imidazolium iodideYield 93.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1.5 g of N-[4-(2-methyl-1H-imidazol-1-yl)phenyl]-4-(tetradecyloxy)benzeneacetamide and 2.11 g of methyl iodide in 25 ml of toluene is refluxed under argon for 2 hours, cooled, diluted with ether and the solid collected. The cake is dried to give 1.8 g of the desired product as a white solid, m.p. 140°-143° C.

Workup

  1. temperatureis refluxed under argon for 2 hours
  2. temperaturecooled
  3. customthe solid collected
  4. customThe cake is dried

Sources & evidence

ORD record
ord-5e7d16dcfe5c42f28275a91f1461e4eb
Source dataset
uspto-grants-1993_07
Patent number
US05231182

Reaction notes

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