Dimethyl(methylene)ammounium iodide → HCID 69106754, compound

HRID 2113443Notes

Reaction equation

HRID 2113443 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=2[C:9]#[N:10])[CH:6]=1.[CH3:18][N+:19]([CH3:21])=[CH2:20].[I-]>CN(C=O)C>[CH3:18][N:19]([CH2:21][C:6]1[N:5]([C:7]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=2[C:9]#[N:10])[CH:4]=[N:3][C:2]=1[CH3:1])[CH3:20]

Participants

4

Reactant 2

HCID 2724133Dimethyl(methylene)ammounium iodideHCID 66885651HCID 66885651, compound

Product 1

HCID 69106754HCID 69106754, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to example 5b, 2-(4-methyl-imidazol-1-yl)-5-nitro-benzonitrile (+regioisomer) was reacted with Eschenmoser's salt in DMF for 16 h at 90° C. Evaporation of the solvent, aqueous workup and chromatography afforded the title compound as a yellow oil that was sufficiently pure to be used in the next step (yield: 35%). MS: m/e=286.1 [M+H]+.

Workup

  1. customEvaporation of the solvent, aqueous workup and chromatography

Sources & evidence

ORD record
ord-4ce666697c28468b8aacdbdb1f96750a
Source dataset
uspto-grants-2008_10
Patent number
US07432256B2

Reaction notes

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