Triethylsilane → HCID 57743078, compound

HRID 1924253Notes

Reaction equation

HRID 1924253 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][N:6]([CH3:13])[C:7]=1[C:8](=[O:12])SCC)#[N:2].C([SiH](CC)CC)C>CC(C)=O.[Pd]>[CH:8]([C:7]1[N:6]([CH3:13])[CH:5]=[N:4][C:3]=1[C:1]#[N:2])=[O:12]

Participants

5

Reactant 2

HCID 12052Triethylsilane2×HCID 53629164HCID 53629164, compound

Product 1

HCID 57743078HCID 57743078, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

In a 750 ml, three-necked flask fitted with a magnetic stirrer under inert atmosphere, S-ethyl 4-cyano-1-methyl-1H-imidazole-5-carbothioate x85 (8 g, 0.041 mol) is dissolved in 400 ml of acetone. Pd on charcoal (1.6 g) is added and the mixture is cooled to 0° C. Triethylsilane (13.1 ml, 0.082 mol) is added dropwise and the mixture is stirred at 0° C. for 0.5 h. The reaction is monitored by NMR. Three additional portions of triethylsilane (0.041 mol, 0.041 mol and 0.0205 mol) are added over a period of 14 h, 17 h and 19 h respectively while stirring at 0° C. The mixture is filtered on Celite after complete consumption of starting product. The solvent is evaporated and the residue is purified twice by chromatography on silicagel (Hexane/AcOEt:6/4 (v/v)) to afford 3 g of 5-formyl-1-methyl-1H-imidazole-4-carbonitrile x86.

Workup

  1. stirringwhile stirring at 0° C
  2. filtrationThe mixture is filtered on Celite
  3. customafter complete consumption of starting product
  4. customThe solvent is evaporated
  5. customthe residue is purified twice by chromatography on silicagel (Hexane/AcOEt:6/4 (v/v))

Sources & evidence

ORD record
ord-1ffad1c11f7c48abbbd7cc7720391f3c
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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