Dimethyl(methylene)ammounium iodide → 2-(5-Dimethylaminomethyl-4-methyl-imidazol-1-yl)-5-trifluoromethoxy-benzonitrile

HRID 2113448Notes

Reaction equation

HRID 2113448 reaction equation
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]2)=[C:8]([CH:11]=1)[C:9]#[N:10].[CH3:20][N+:21]([CH3:23])=[CH2:22].[I-]>CN(C=O)C>[CH3:20][N:21]([CH2:23][C:16]1[N:12]([C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:18])[F:19])=[CH:11][C:8]=2[C:9]#[N:10])[CH:13]=[N:14][C:15]=1[CH3:17])[CH3:22]

Participants

4

Reactant 2

HCID 2724133Dimethyl(methylene)ammounium iodideHCID 675493282-(4-Methyl-imidazol-1-yl)-5-trifluoromethoxy benzonitrile

Product 1

HCID 675497602-(5-Dimethylaminomethyl-4-methyl-imidazol-1-yl)-5-trifluoromethoxy-benzonitrileYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to example 5b, 5-trifluoromethoxy-2-(4-methyl-imidazol-1-yl)-benzonitrile (+regioisomer) was reacted with Eschenmoser's salt in DMF for 24 h at 90° C. Evaporation of the solvent, aqueous workup and chromatography afforded the title compound as a colorless oil that was sufficiently pure to be used in the next step (yield: 38%). 1H-NMR (300 MHz, DMSO): δ=1.93 (s, 6H), 2.17 (s, 3H), 3.21 (s, 2H), 7.80-7.95 (m, 3H), 8.22 (s, 1H).

Workup

  1. customEvaporation of the solvent, aqueous workup and chromatography

Sources & evidence

ORD record
ord-00489ff7b91142ed817457fb253a448f
Source dataset
uspto-grants-2008_10
Patent number
US07432256B2

Reaction notes

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