Dimethylformamide → HCID 54500603, compound

HRID 358842Notes

Reaction equation

HRID 358842 reaction equation
CN(C=O)C.[C:6]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1I)(=[O:8])[CH3:7].[C:18]([OH:22])(=[O:21])[CH:19]=[CH2:20].C([O-])(=O)C.[Na+]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[C:6]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[CH:20]=[CH:19][C:18]([OH:22])=[O:21])(=[O:8])[CH3:7]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 6581Acrylic AcidHCID 517045Sodium AcetateHCID 15113903N-(4-chloro-2-iodophenyl)acetamide

Product 1

HCID 54500603HCID 54500603, compoundYield 85.7%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

To a 200-ml flask were added 40 ml of DMF, 20 g (0.0677 mole) of 2-acetylamino-5-chloroiodobenzene, 5.85 g (0.0812 mole) of acrylic acid, 7.77 g (0.0947 mole) of anhydrous sodium acetate, 10 mg of palladium chloride and 30 mg of triphenylphosphine. This mixture was stirred at 115° C. for 5 hours and poured into 200 ml of water, and then a large amount of crystal precipitated. Sodium hydroxide was added to this aqueous solution containing the crystal while stirring the solution as it was, until the pH of the solution became 9.0. Then, the crystal dissolved in the solution to obtain a uniform solution. Thereafter, 2 g of activated carbon was added to the solution, and after stirring at room temperature for 15 minutes, the insoluble matter was filtered off. The filtrate was acidified to a pH of 1.5 with conc. hydrochloric acid, and then white crystal precipitated. This crystal was filtered off and vacuum-dried to obtain 13.9 g of 2-acetylamino-5-chlorocinnamic acid. The yield was 85.2% of the theoretical value, and the melting point was 243° to 245° C. The 1H-NMR and IR of this compound were as follows:

Workup

  1. customa large amount of crystal precipitated
  2. additionSodium hydroxide was added to this aqueous solution
  3. additioncontaining the crystal
  4. stirringwhile stirring the solution as it
  5. dissolutionThen, the crystal dissolved in the solution
  6. customto obtain a uniform solution
  7. additionThereafter, 2 g of activated carbon was added to the solution
  8. stirringafter stirring at room temperature for 15 minutes
  9. filtrationthe insoluble matter was filtered off
  10. customwhite crystal precipitated
  11. filtrationThis crystal was filtered off
  12. customvacuum-dried

Sources & evidence

ORD record
ord-dbac2e19be34477a961b82b2cff056d1
Source dataset
uspto-grants-1991_03
Patent number
US04997972

Reaction notes

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