Acetone → 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrile

HRID 1711224Notes

Reaction equation

HRID 1711224 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]#[N:7])[N:3]=[CH:2]1.[CH3:8][Si:9]([CH3:16])([CH3:15])[CH2:10][CH2:11][O:12][CH2:13]Cl.C([O-])([O-])=O.[K+].[K+].CC(C)=O>CCOC(C)=O>[CH3:8][Si:9]([CH3:16])([CH3:15])[CH2:10][CH2:11][O:12][CH2:13][N:1]1[CH:5]=[C:4]([C:6]#[N:7])[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178510437HCID 178510437, compound

Product 1

HCID 584311371-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrileYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A flask charged with imidazole-4-carbonitrile (0.50 g, 5.2 mmol) (Synthesis, 677, 2003), 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl) (0.95 mL, 5.3 mmol), K2CO3 (1.40 g, 10.4 mmol), and acetone (5 mL) was stirred for 10 h at RT. The mixture was diluted with EtOAc (20 mL) and washed with water (20 mL) and brine (20 mL) and the organic layer dried over MgSO4. The crude product was eluted from a 20-g SPE cartridge (silica) with 30% EtOAc/hexane to give 0.80 g (70%) of the title compound as a colorless oil. Mass spectrum (CI (CH4), m/z) Calcd. for C10H17N3OSi, 224.1 (M+H), found 224.1.

Workup

  1. washwashed with water (20 mL) and brine (20 mL)
  2. dry with materialthe organic layer dried over MgSO4
  3. washThe crude product was eluted from a 20-g SPE cartridge (silica) with 30% EtOAc/hexane

Sources & evidence

ORD record
ord-c40abb2f7639438386cbf4bb5e857881
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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