Dimethyl(methylene)ammounium iodide → HCID 69106626, compound

HRID 2113464Notes

Reaction equation

HRID 2113464 reaction equation
[F:1][C:2]1[C:3]([N:10]2[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[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:3]2[C:2]([F:1])=[CH:9][CH:8]=[CH:7][C:4]=2[C:5]#[N:6])[CH:11]=[N:12][C:13]=1[CH3:15])[CH3:18]

Participants

4

Reactant 2

HCID 2724133Dimethyl(methylene)ammounium iodideHCID 69106680HCID 69106680, compound

Product 1

HCID 69106626HCID 69106626, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to example 5b, 3-fluoro-2-(4-methyl-imidazol-1-yl)-benzonitrile was reacted with Eschenmoser's salt in DMF for 16 h at 90° C. Evaporation of the solvent, aqueous workup and chromatography (SiO2, dichloromethane:methanol=100:0 to 98:2) afforded the title compound as a light yellow oil (yield: 13%). 1H-NMR (400 MHz, DMSO): δ=1.91 (s, 6H), 2.17 (s, 3H), 3.17 (s, 2H), 7.72-7.92 (m, 4H)

Workup

  1. customEvaporation of the solvent, aqueous workup and chromatography (SiO2, dichloromethane:methanol=100:0 to 98:2)

Sources & evidence

ORD record
ord-47caaaac154e44f89ebc34df599e9938
Source dataset
uspto-grants-2008_10
Patent number
US07432256B2

Reaction notes

Loading…