Acetanilide → HCID 21998426, compound

HRID 1976520Notes

Reaction equation

HRID 1976520 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=O)[CH3:2].[C:11](=[O:14])([O-])[O-:12].[K+].[K+].[OH-].[K+]>S([O-])([O-])(=O)=O.[Cu+2].CO>[CH2:11]1[O:14][C:6]2[CH:5]=[CH:10][C:1]([NH:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:2][C:7]=2[O:12]1

Participants

6

Reactant 3

HCID 904AcetanilideHCID 11430Potassium CarbonateHCID 14797Potassium Hydroxide

Product 1

HCID 21998426HCID 21998426, compoundYield 167.1%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 887MethanolSolvent

Procedure

A mixture of 90 g (0.448 mol) of 3,4-bromomethylenedioxybenzene, 50 g (0.37 mol) of acetanilide, 12 g (0.075 mol) of copper sulfate, and 80 g (0.579 mol) of potassium carbonate was reacted in the same manner as in Example 5 (2) to obtain a crude reaction product. A mixture of this crude product, 121.4 g (1.84 mol) of 85% KOH, and 200 ml of methanol was refluxed overnight and then concentrated. Water was added thereto. The resultant mixture was extracted with toluene twice. The toluene phase was washed with water three times, dried, and then concentrated. The residue was distilled under vacuum to obtain 65.91 g of N-3,4-methylenedioxyphenyl-N-phenylamine.

Workup

  1. customto obtain a crude
  2. customreaction product
  3. temperaturewas refluxed overnight
  4. concentrationconcentrated
  5. additionWater was added
  6. extractionThe resultant mixture was extracted with toluene twice
  7. washThe toluene phase was washed with water three times
  8. customdried
  9. concentrationconcentrated
  10. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-98fe596881c64463b5ab0a7d67c397a3
Source dataset
uspto-grants-2001_05
Patent number
US06228547B1

Reaction notes

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