Imidazole → HCID 14419323, compound

HRID 1808670Notes

Reaction equation

HRID 1808670 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].I[CH2:9][CH2:10][CH2:11][Si:12]([O:17][CH3:18])([O:15][CH3:16])[O:13][CH3:14].ClCCl>O1CCCC1>[CH3:14][O:13][Si:12]([CH2:11][CH2:10][CH2:9][C:2]1[NH:1][CH:5]=[CH:4][N:3]=1)([O:17][CH3:18])[O:15][CH3:16]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 2759373(3-Iodopropyl)trimethoxysilane

Product 1

HCID 14419323HCID 14419323, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5 g (73 mmol) of imidazole were dissolved in 100 ml of tetrahydrofurane and 1.73 g (73 mmol) of sodium hydride were added. The suspension was stirred for 4 hours, after which 10 ml of iodopropyltrimethoxy silane (52 mmol) were added and the reaction mixture was heated under reflux for 18 hours. 15 ml of dichloromethane were then added and the reaction mixture was filtered. The filtrate was concentrated under reduced pressure and the product was distilled off at 150-155° C. at 8 mbar. The yield was 8.2 g (60%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 18 hours
  3. filtrationthe reaction mixture was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. distillationthe product was distilled off at 150-155° C. at 8 mbar

Sources & evidence

ORD record
ord-38adc40401b7427a9df5599cad9438fb
Source dataset
uspto-grants-2013_01
Patent number
US08361627B2

Reaction notes

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