Methyl iodide → 2-[5-(N-acetyl-N-methylamino)-2-methoxyphenyl]-1,3-dioxolane

HRID 356640Notes

Reaction equation

HRID 356640 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([O:16][CH3:17])=[C:9]([CH:11]2[O:15][CH2:14][CH2:13][O:12]2)[CH:10]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH3:20]I.[Cl-].[NH4+]>CN(C=O)C>[C:1]([N:4]([C:5]1[CH:6]=[CH:7][C:8]([O:16][CH3:17])=[C:9]([CH:11]2[O:15][CH2:14][CH2:13][O:12]2)[CH:10]=1)[CH3:20])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 189389762-(5-Acetylamino-2-methoxyphenyl)-1,3-dioxolane

Product 1

HCID 189389782-[5-(N-acetyl-N-methylamino)-2-methoxyphenyl]-1,3-dioxolaneYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-(5-acetylamino-2-methoxyphenyl)-1,3-dioxolane (5.0 g, 21.1 mmol) in DMF (16 ml) was added to a suspension of NaH (1.0 g, 25.3 mmol) in DMF (5 ml) and then the mixture was stirred at room temperature for 10 min. To the mixture was added methyl iodide (3.6 g, 25.3 mmol) and then stirred at room temperature for 1 hr. And to the resulted reaction mixture was added ammonium chloride and then extracted with CH2Cl2. The extract was washed with water and brine, dried over Na2SO4 and concentrated in vacuo to give crude 2-[5-(N-acetyl-N-methylamino)-2-methoxyphenyl]-1,3-dioxolane (5.0 g, 94%) as a orange oil.

Workup

  1. stirringstirred at room temperature for 1 hr
  2. customAnd to the resulted reaction mixture
  3. extractionextracted with CH2Cl2
  4. washThe extract was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f338adb2b4f0471a95c94330f5790095
Source dataset
uspto-grants-1998_11
Patent number
US05837711

Reaction notes

Loading…