Methanol → N-(m-ethylphenyl)-N-ethylcyanamide

HRID 1069170Notes

Reaction equation

HRID 1069170 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+].[CH2:14](Br)[CH3:15].CO>C1COCC1.O>[CH2:1]([C:3]1[CH:4]=[C:5]([N:9]([CH2:14][CH3:15])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1)[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 10012043[(3-Ethylphenyl)amino]carbonitrile

Product 1

HCID 10442201N-(m-ethylphenyl)-N-ethylcyanamideYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
82.5 °C

Procedure

A suspension of m-ethylphenylcyanamide (2.26 g, 15.45 mmol) and sodium hydride (820 mg, 34.2 mmol, pre-washed thrice with hexane) in anhydrous THF (20 ml) was heated at 80-85° C. for 2.5 hours. After it was allowed to cool to room temperature ethyl bromide (4.66 g, 42.76 mmol) was added and continued stirring at room temperature for 6 hours. Methanol (20 ml) followed by water (40 ml) were added and then extracted with dichloromethane (3×25 ml). Concentration of the organic layer followed by quick flash chromatography afforded the title compound (2.36 mg, 88%) as a light yellow liquid:

Workup

  1. additionwas added
  2. additionwere added
  3. extractionextracted with dichloromethane (3×25 ml)

Sources & evidence

ORD record
ord-b586563c445344e494e7c6e67eac26b3
Source dataset
uspto-grants-2001_06
Patent number
US06251948B1

Reaction notes

Loading…