Trimethylsilyl cyanide → HCID 178424683, compound

HRID 1488104Notes

Reaction equation

HRID 1488104 reaction equation
C[Si](C)(C)[C:3]#[N:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O[CH2:26][C:27]1[NH:28][C:29]([C:33]2[C:34]([CH3:43])=[CH:35][C:36]([CH3:42])=[C:37]([CH:41]=2)[C:38]([OH:40])=[O:39])=[C:30]([CH3:32])[N:31]=1>C(#N)C>[C:3]([CH2:26][C:27]1[NH:28][C:29]([C:33]2[C:34]([CH3:43])=[CH:35][C:36]([CH3:42])=[C:37]([CH:41]=2)[C:38]([OH:40])=[O:39])=[C:30]([CH3:32])[N:31]=1)#[N:4]

Participants

5

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 178424688HCID 178424688, compound2×

Product 1

HCID 178424683HCID 178424683, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a solution of trimethylsilanecarbonitrile (376 mg, 3.79 mmol) in acetonitrile (20 mL). Tetrabutylammonium fluoride (3.8 mL, 1 M in THF) was added to the reaction. This was followed by the addition of 5-(2-(hydroxymethyl)-4-methyl-1H-imidazol-5-yl)-2,4-dimethylbenzoic acid (compound 222.5, 190 mg, 0.73 mmol), in portions. The reaction mixture was stirred for 1 h at room temperature, then concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:1) as eluent to furnish 190 mg (97%) of the title compound as a yellow solid.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:1) as eluent

Sources & evidence

ORD record
ord-a2b2f99239cd45fa9c80880846b15313
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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