Methyl iodide → HCID 53821345, compound

HRID 1247971Notes

Reaction equation

HRID 1247971 reaction equation
[CH3:1][N:2]([CH3:18])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:17])[CH2:15][CH3:16])=[CH:9][CH:8]=1)=[O:6].[H-].[Na+].[H][H].[CH3:23]I>CN(C)C=O>[CH3:18][N:2]([CH3:1])[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]([N:13]([CH3:23])[C:14](=[O:17])[CH2:15][CH3:16])=[CH:11][CH:12]=1)=[O:6]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53818500N-[4-[3-(Dimethylamino)-1-oxo-2-propen-1-yl]phenyl]propanamideHCID 178418361HCID 178418361, compound

Product 1

HCID 53821345HCID 53821345, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A soluton of 3.10 g of N-[4-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]propanamide in 25 ml dimethylformamide was stirred in an inert atmosphere and 0.60 g of sodium hydride (60% oil suspension) was added. After stirring for 1 hour, the liberation of hydrogen had ceased and a solution of 1.8 g of methyl iodide in 5 ml of dimethylformamide was added portionwise. After stirring for an additional hour, the system was evaporated to remove volatiles and then the reaction mixture was triturated 3 times with hexane (3×50 ml). The reaction mixture was carefully poured into cold water and extracted with methylene chloride. The methylene chloride solution was dried and evaporated to dryness at reduced pressure to yield a crystalline solid. Recrystallization from methylene chloridehexane gave a yellow crystalline solid, mp 76°-78° C.

Workup

  1. additionwas added
  2. stirringAfter stirring for an additional hour
  3. customthe system was evaporated
  4. customto remove volatiles
  5. customthe reaction mixture was triturated 3 times with hexane (3×50 ml)
  6. additionThe reaction mixture was carefully poured into cold water
  7. extractionextracted with methylene chloride
  8. dry with materialThe methylene chloride solution was dried
  9. customevaporated to dryness at reduced pressure
  10. customto yield a crystalline solid
  11. customRecrystallization from methylene chloridehexane
  12. customgave a yellow crystalline solid, mp 76°-78° C.

Sources & evidence

ORD record
ord-f2c6a471483c4ca392a9e7acda1e4172
Source dataset
uspto-grants-1985_06
Patent number
US04521422

Reaction notes

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