Dimethyl(methylene)ammounium iodide → HCID 69106979, compound

HRID 2113456Notes

Reaction equation

HRID 2113456 reaction equation
[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([N:11]2[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]2)[C:3]=1[C:4]#[N:5].[CH3:17][N+:18]([CH3:20])=[CH2:19].[I-]>CN(C=O)C>[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([N:11]2[C:15]([CH2:17][N:18]([CH3:20])[CH3:19])=[C:14]([CH3:16])[N:13]=[CH:12]2)[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 2724133Dimethyl(methylene)ammounium iodideHCID 69106905HCID 69106905, compound

Product 1

HCID 69106979HCID 69106979, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to example 5b, 2-chloro-3-fluoro-6-(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 97:3) afforded the title compound as a light yellow oil (yield: 52%). MS: m/e=293.1 [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-ec96ac7ab4f8406f82a9abbcc38a39ac
Source dataset
uspto-grants-2008_10
Patent number
US07432256B2

Reaction notes

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