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

HRID 536914Notes

Reaction equation

HRID 536914 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), washed with water (20 mL), brine (20 mL) and the organic layer was 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), brine (20 mL)
  2. dry with materialthe organic layer was 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-0f53db526cf64d9ba0883f19f311e6af
Source dataset
uspto-grants-2014_10
Patent number
US08859602B2

Reaction notes

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