Dimethyl(methylene)ammounium iodide → HCID 68406409, compound

HRID 1786226Notes

Reaction equation

HRID 1786226 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]2)[C:3]=1[C:4]#[N:5].[CH3:16][N+:17]([CH3:19])=[CH2:18].[I-]>CN(C=O)C>[CH3:16][N:17]([CH2:19][C:14]1[N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[C:3]=2[C:4]#[N:5])[CH:11]=[N:12][C:13]=1[CH3:15])[CH3:18]

Participants

4

Reactant 2

HCID 2724133Dimethyl(methylene)ammounium iodideHCID 67549351HCID 67549351, compound

Product 1

HCID 68406409HCID 68406409, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

As described for example 84b, 2-fluoro-6-(4-methyl-imidazol-1-yl)-benzonitrile was reacted with Eschenmoser's salt in DMF for 7 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 solid (yield: 46%). 1H-NMR (400 MHz, DMSO): δ=1.94 (s, 6H), 2.17 (s, 3H), 3.23 (s, 2H), 7.61-7.67 (m, 2H), 7.86 (s, 1H), 7.86-7.96 (m, 1H).

Workup

  1. customEvaporation of the solvent, aqueous workup and chromatography (SiO2, dichloromethane:methanol=100:0 to 97:3)

Sources & evidence

ORD record
ord-df2a07e78d594c3eb949a2ed98043806
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

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