Dimethyl(methylene)ammounium iodide → HCID 67549239, compound

HRID 1786208Notes

Reaction equation

HRID 1786208 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8].[CH3:16][N+:17]([CH3:19])=[CH2:18].[I-]>CN(C=O)C>[CH3:16][N:17]([CH2:19][C:14]1[N:10]([C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:9][C:6]=2[C:7]#[N:8])[CH:11]=[N:12][C:13]=1[CH3:15])[CH3:18]

Participants

4

Reactant 2

HCID 2724133Dimethyl(methylene)ammounium iodideHCID 67548761HCID 67548761, compound

Product 1

HCID 67549239HCID 67549239, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

As described for example 84b, 5-iodo-2-(4-methyl-imidazol-1-yl)-benzonitrile (+regioisomer) was reacted with Eschenmoser's salt in DMF for 72 h at 90° C. Evaporation of the solvent, aqueous workup and chromatography (SiO2, dichloromethane:methanol=100:0 to 97:3) afforded the title compound as a white solid (yield: 38%). MS: m/e=367.0 [M+H]+.

Workup

  1. customEvaporation of the solvent, aqueous workup and chromatography (SiO2, dichloromethane:methanol=100:0 to 97:3)

Sources & evidence

ORD record
ord-f7e99499be19427c84b15411463fc75a
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

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