Dimethyl(methylene)ammounium iodide → HCID 67549380, compound

HRID 2113441Notes

Reaction equation

HRID 2113441 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([N:11]2[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]2)=[C:7]([CH:10]=1)[C:8]#[N:9].[CH3:19][N+:20]([CH3:22])=[CH2:21].[I-]>CN(C=O)C>[F:18][C:2]([F:1])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([N:11]2[C:15]([CH2:19][N:20]([CH3:22])[CH3:21])=[C:14]([CH3:16])[N:13]=[CH:12]2)=[C:7]([CH:10]=1)[C:8]#[N:9]

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

In analogy to example 5b, 5-trifluoromethyl-2-(4-methyl-imidazol-1-yl)-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-32a187cb0a57488fa31135a7ac3801eb
Source dataset
uspto-grants-2008_10
Patent number
US07432256B2

Reaction notes

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