Methyl iodide → HCID 54462077, compound

HRID 1906840Notes

Reaction equation

HRID 1906840 reaction equation
[CH3:1][N:2]([CH3:19])[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[C:9]([NH:13][C:14]([CH:16]2[CH2:18][CH2:17]2)=[O:15])[CH:10]=[CH:11][CH:12]=1)=[O:6].[H-].[Na+].[CH3:22]I>CN(C)C=O>[CH3:19][N:2]([CH3:1])[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[C:9]([N:13]([CH3:22])[C:14]([CH:16]2[CH2:17][CH2:18]2)=[O:15])[CH:10]=[CH:11][CH:12]=1)=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54261313HCID 54261313, compound

Product 1

HCID 54462077HCID 54462077, compoundYield 654.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 10.33 g of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]cyclopropanecarboxamide and 1.92 g of 60% sodium hydride in oil in 50 ml of dimethylformamide was stirred for one hour under argon, then cooled in an ice bath. A solution of 0.81 g of methyl iodide in 10 ml of dimethylformamide was added dropwise. The mixture was then stirred at room temperature for 0.5 hour and extracted three times with hexane. The mixture was diluted with water and this mixture extracted with dichloromethane. This extract was evaporated and the residue crystallized from hexane, giving 10.17 g of the desired compound, mp 120°-122° C.

Workup

  1. temperaturecooled in an ice bath
  2. stirringThe mixture was then stirred at room temperature for 0.5 hour
  3. extractionextracted three times with hexane
  4. additionThe mixture was diluted with water
  5. extractionthis mixture extracted with dichloromethane
  6. customThis extract was evaporated
  7. customthe residue crystallized from hexane

Sources & evidence

ORD record
ord-d35330ddebc448db8aff9ddae483e3ba
Source dataset
uspto-grants-1987_03
Patent number
US04654347

Reaction notes

Loading…