Sodium Iodide → Naproxennndiethylglycolamideester

HRID 1461119Notes

Reaction equation

HRID 1461119 reaction equation
[CH3:1][C@H:2]([C:15]([OH:17])=[O:16])[C:3]1[CH:4]=[CH:5][C:6]2[CH:7]=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][C:11]=2[CH:12]=1.Cl[CH2:19][C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21].C(N(CC)CC)C.[I-].[Na+]>CN(C)C=O.O>[CH3:14][O:13][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[CH:12]=[C:3]([CH:2]([CH3:1])[C:15]([O:17][CH2:19][C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21])=[O:16])[CH:4]=[CH:5]2

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 16844Chloro-N,N-diethylacetamideHCID 156391Naproxen

Product 1

HCID 23276569NaproxennndiethylglycolamideesterYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Naproxen (1.07 g, 5 mmole) and 2-chloro-N,N-diethyl-acetamide (0.90 g, 6 mmole) were dissolved in 7 ml of N,N-dimethylformamide and triethylamine (1.4 ml, 10 mmole) and sodium iodide (76 mg) were added. The mixture was refluxed for 2 h, cooled and poured into 35 ml of water. The precipitate formed after standing overnight at 4° C. was collected by filtration, washed with water and recrystalized from 95% ethanol, yielding 1.5 g (92%) of the title compound. Mp 89°-89.5° C.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. temperaturecooled
  3. customThe precipitate formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customrecrystalized from 95% ethanol

Sources & evidence

ORD record
ord-f2be9c6898544ee1a62c688f3f2dc8fd
Source dataset
uspto-grants-1991_12
Patent number
US05073641

Reaction notes

Loading…