Methyl iodide → HCID 86744501, compound

HRID 1494186Notes

Reaction equation

HRID 1494186 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH:13]([CH3:28])[C:14]([O:16][CH2:17][CH2:18][NH:19][C:20]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)=[O:21])=[O:15])=[CH:8][CH:7]=[CH:6]2.[CH3:29][I:30]>CC(C)=O>[I-:30].[CH3:29][N+:24]1[CH:25]=[CH:26][CH:27]=[C:22]([C:20](=[O:21])[NH:19][CH2:18][CH2:17][O:16][C:14](=[O:15])[CH:13]([CH3:28])[C:9]2[C:10]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:23]=1

Participants

4

Reactant 2

HCID 6328Methyl iodide2×HCID 86744689HCID 86744689, compound

Product 1

HCID 86744501HCID 86744501, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The quaternization of the naproxen ester prepared in Example 92 (1.0 g, 2.6 mmol) was carried out using methyl iodide (2.3 g, 16 mmol) in acetone (45 mL). The solution was heated to reflux for 20 hours. Methyl iodide (1.1 g, 8.0 mmol) was again added to the reaction flask. The precipitated product was filtered after an additional 4 hours of reaction time. The off-white powder was dried. The material weighed 2.2 g and was found to be analytically pure without recrystallization. The solvent was removed from the acetone filtrate and the residue was solidified with anhydrous ether. The resulting dark yellow powder was dissolved in water and washed with ether (4×30 mL). The water was then removed under vacuum giving 0.2 g of a lighter yellow powder. The overall yield of the reaction was 93%; mp 169°-170° C. The product had the structural formula ##STR123## as further confirmed by UV, NMR and elemental analyses.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 20 hours
  3. filtrationThe precipitated product was filtered after an additional 4 hours of reaction time
  4. customThe off-white powder was dried
  5. customto be analytically pure without recrystallization
  6. customThe solvent was removed from the acetone filtrate
  7. dissolutionThe resulting dark yellow powder was dissolved in water
  8. washwashed with ether (4×30 mL)
  9. customThe water was then removed under vacuum
  10. customgiving 0.2 g of a lighter yellow powder

Sources & evidence

ORD record
ord-a3e806b548ff4e779a348170b7325b22
Source dataset
uspto-grants-1991_06
Patent number
US05024998

Reaction notes

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