Sodium Iodide → HCID 21409856, compound

HRID 1283553Notes

Reaction equation

HRID 1283553 reaction equation
[CH3:1][NH:2][C:3]([CH3:15])([CH3:14])[CH2:4][NH:5][C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.BrC[CH:18]=[C:19]([CH3:21])[CH3:20].[C:22](=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CC(CC)=O>[CH3:14][C:3]([N:2]([CH3:22])[CH2:1][CH:18]=[C:19]([CH3:21])[CH3:20])([CH3:15])[CH2:4][NH:5][C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 21409819N-[2-Methylamino-2-methylpropyl]benzamide

Product 1

HCID 21409856HCID 21409856, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

A solution of N[2-methylamino-2-methylpropyl]benzamide (1 g., 0.0052 mole) in methylethyl ketone (MEK) (25 ml.) was added to a solution of 1-bromo-3-methyl-but-2-ene (0.78 g., 0.0052 mole) in MEK (40 ml.) containing sodium carbonate (0.55 g., 0.0052 mole) and a few crystals of sodium iodide. The mixture was heated under reflux for 30 hrs. The inorganic solids were filtered off and the filtrant concentrated by evaporation under reduced pressure to give a liquid residue. This was loaded onto an alumina column and eluted with ethyl acetate. Fractions (25 mls) were collected and concentrated to give N[2-methyl-2[methyl(3-methyl-2-butenyl)amino]propyl]benzamide (1.2 g.).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 hrs
  3. filtrationThe inorganic solids were filtered off
  4. concentrationthe filtrant concentrated by evaporation under reduced pressure
  5. customto give a liquid residue
  6. washeluted with ethyl acetate
  7. customFractions (25 mls) were collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-62d7e25e5a1c416489d600efbafdd07a
Source dataset
uspto-grants-1976_08
Patent number
US03975443

Reaction notes

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