Methanol → m-ethylphenyl-N-methylcyanamide

HRID 482567Notes

Reaction equation

HRID 482567 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1)[CH3:2].[H-].[Na+].[CH3:14]I.CO>C1COCC1.O>[CH2:1]([C:3]1[CH:4]=[C:5]([N:9]([CH3:14])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1)[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10012043[(3-Ethylphenyl)amino]carbonitrile

Product 1

HCID 10103434m-ethylphenyl-N-methylcyanamideYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of m-ethylphenylcyanamide (1.46 g, 10 mmol) and sodium hydride (480 mg, 20 mmol, pre-washed thrice with hexane) in anhydrous THF (10 ml) was heated at 80°-85° C. for 2.5 hours. After it was allowed to cool to room temperature, methyl iodide (3.5 g, 25 mmol) was added and stirring continued at room temperature for 2 hours. Methanol (10 ml) followed by water (20 ml) was added and the reaction mixture was extracted with dichloromethane (3×25 ml). Concentration of the organic layer followed by flash chromatography on SiO2 afforded N-(m-ethylphenyl)-N-methylcyanamide (960 mg, 60%) as a colorless liquid: IR (film): 2220, 3400 cm-1.

Workup

  1. additionwas added
  2. extractionthe reaction mixture was extracted with dichloromethane (3×25 ml)

Sources & evidence

ORD record
ord-fda1c14bf8ec48878c004edb1ca7b665
Source dataset
uspto-grants-1998_08
Patent number
US05798390

Reaction notes

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