Methyl iodide → HCID 64865760, compound

HRID 1591746Notes

Reaction equation

HRID 1591746 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][C:14](=O)OCC2C=CC=CC=2)=[CH:7][CH:6]=1)#[N:4].CI>O1CCCC1>[CH3:14][NH:13][CH2:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]([C:3]#[N:4])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12030671HCID 12030671, compound

Product 1

HCID 64865760HCID 64865760, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

With ice bath cooling, 0.43 g (17.03 mmol) of sodium hydride (95%) was added to a solution of 3.183 g (11.36 mmol) of benzyl [2-(4-cyanophenyl)ethyl]carbamate in 70 ml of tetrahydrofuran. The mixture was stirred for a further 5 minutes with cooling and at room temperature for 10 minutes. 1.06 ml (17.03 mmol) of methyl iodide were then added to the reaction mixture, which was subsequently stirred at room temperature overnight. With ice bath cooling, the mixture was then quenched with water and extracted with ethyl acetate. The organic extracts were washed with saturated sodium chloride solution, dried over sodium sulphate and evaporated to dryness. The product obtained in this manner was reacted further without additional purification.

Workup

  1. temperatureWith ice bath cooling
  2. stirringwas subsequently stirred at room temperature overnight
  3. temperatureWith ice bath cooling
  4. customthe mixture was then quenched with water
  5. extractionextracted with ethyl acetate
  6. washThe organic extracts were washed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. customevaporated to dryness
  9. customThe product obtained in this manner
  10. customwas reacted further without additional purification

Sources & evidence

ORD record
ord-fd5449f496344546b2b9d1a5bd642b6c
Source dataset
uspto-grants-2007_11
Patent number
US07291642B2

Reaction notes

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