Dimethyl(methylene)ammounium iodide → HCID 67549380, compound

HRID 1786213Notes

Reaction equation

HRID 1786213 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:8]=2[C:9]#[N:10])[CH:6]=1.[CH3:19][N+:20]([CH3:22])=[CH2:21].[I-]>CN(C=O)C>[CH3:19][N:20]([CH2:22][C:6]1[N:5]([C:7]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:11][C:8]=2[C:9]#[N:10])[CH:4]=[N:3][C:2]=1[CH3:1])[CH3:21]

Participants

4

Reactant 2

HCID 2724133Dimethyl(methylene)ammounium iodideHCID 68406249HCID 68406249, compound

Product 1

HCID 67549380HCID 67549380, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

As described for example 84b, 2-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-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: 53%). MS: m/e=309.3 [M+H]+.

Workup

  1. customEvaporation of the solvent, aqueous workup and chromatography

Sources & evidence

ORD record
ord-c28d8651a79042e48de28c766b8131d8
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

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