Dimethylformamide → Methyl 2-acetamido-5-chlorocinnamate

HRID 358841Notes

Reaction equation

HRID 358841 reaction equation
CN(C)C=O.[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]([O:22][CH3:23])(=[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]([O:22][CH3:23])=[O:21])(=[O:8])[CH3:7]

Participants

8

Reactant 4

HCID 6228Dimethylformamide2×HCID 7294Methyl AcrylateHCID 517045Sodium AcetateHCID 15113903N-(4-chloro-2-iodophenyl)acetamide

Product 1

HCID 54287744Methyl 2-acetamido-5-chlorocinnamateYield 82.2%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent

Procedure

To a 200-ml flask were successively charged 40 ml of N,N-dimethylformamide (hereinafter abbreviated as DMF), 20 g (0.0677 mole) of 2-acetylamino-5-chloroiodobenzene, 5.94 g (0.069 mole) of methyl acrylate, 6.94 g (0.0846 mole) of anhydrous sodium acetate, 10 mg of palladium chloride and 30 mg of triphenylphosphine in this order. This mixture was stirred at 130° to 135° C. for 3 hours and poured into 200 ml of water, and then a large amount of crystal precipitated. This crystal was filtered off, thoroughly washed with water and dried in vacuo to obtain 14.1 g of methyl 2-acetylamino-5-chlorocinnamate. The yield was 82.2% of the theoretical value, and the melting point was 172° to 174° C. The nuclear magnetic resonance spectrum (1H-NMR) and infrared absorption spectrum (IR) of this compound were as follows:

Workup

  1. customTo a 200-ml flask were successively charged
  2. customa large amount of crystal precipitated
  3. filtrationThis crystal was filtered off
  4. washthoroughly washed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-84b9dc96ea844d439a675cf35e96d33c
Source dataset
uspto-grants-1991_03
Patent number
US04997972

Reaction notes

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