Water → HCID 23508546, compound

HRID 1883674Notes

Reaction equation

HRID 1883674 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[O:8])=[CH:5][CH:4]=1.[H-].[Na+].[CH2:22](I)[CH3:23].O>CS(C)=O>[CH2:22]([N:9]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[C:7](=[O:8])[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][CH:18]=1)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 3468154-Methoxy-N-(4-methoxyphenyl)benzamide

Product 1

HCID 23508546HCID 23508546, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture composed of 600 mg of 4-methoxy-N-(4-methoxy-phenyl)benzamide and 150 mg of 60% sodium hydride was stirred in 7.5 ml of dimethyl sulfoxide at 50° C. for 10 minutes. Then, 1.05 ml of ethyl iodide was added, and the reaction mixture was stirred for 30 minutes. After water was added to the reaction mixture, the product was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. After the solvent was distilled off, the resulting crude product was purified by TLC (using a 80:1 mixture of chloroform and acetone as the developing solvent) to obtain 591 mg of N-ethyl-4-methoxy-N-(4-methoxyphenyl)benzamide.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationAfter the solvent was distilled off
  5. customthe resulting crude product was purified by TLC (
  6. additiona 80:1 mixture of chloroform and acetone as the developing solvent)

Sources & evidence

ORD record
ord-492c8d4c3da241919cfaef9dbab8a747
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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