Methyl iodide → HCID 21280977, compound

HRID 542939Notes

Reaction equation

HRID 542939 reaction equation
[H-].[Na+].[C:3]([NH:6][C:7]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([CH3:15])=[CH:9][C:8]=1[O:16][CH3:17])(=[O:5])[CH3:4].[CH3:18]I>CN(C)C=O>[CH3:17][O:16][C:8]1[CH:9]=[C:10]([CH3:15])[CH:11]=[C:12]([O:13][CH3:14])[C:7]=1[N:6]([CH3:18])[C:3](=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21280974HCID 21280974, compound

Product 1

HCID 21280977HCID 21280977, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 12.0 g. of sodium hydride (50% dispersion in oil) in 50 ml. of absolute dimethylformamide was treated with a solution of 46.0 g. of 4-acetamido-3,5-dimethoxy-toluene in 200 ml. of absolute dimethylformamide over a period of 30 minutes with stirring and exclusion of moisture. After stirring at room temperature for 4 hours, 31.2 ml. of methyl iodide were added dropwise over a period of 20 minutes with stirring and ice-cooling. The mixture was stirred at room temperature for 70 hours and subsequently evaporated to dryness under vacuum. The residue was treated with 300 ml. of water and the resulting suspension was extracted with two 500 ml. portions of ethyl acetate. The combined ethyl acetate extracts were washed with 300 ml. of water, dried over magnesium sulfate, filtered and evaporated under vacuum. Recrystallization of the residue from ethyl acetate gave 3,5-dimethoxy-4-(N-methyl-acetamido)-toluene having a melting point of 160°-161° C.

Workup

  1. additionA suspension of 12.0 g
  2. stirringwith stirring
  3. temperatureice-cooling
  4. stirringThe mixture was stirred at room temperature for 70 hours
  5. customsubsequently evaporated to dryness under vacuum
  6. additionThe residue was treated with 300 ml
  7. extractionof water and the resulting suspension was extracted with two 500 ml
  8. washThe combined ethyl acetate extracts were washed with 300 ml
  9. dry with materialof water, dried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated under vacuum
  12. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-ba5c736110c24687a47c307790356431
Source dataset
uspto-grants-1987_04
Patent number
US04659818

Reaction notes

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