Sodium Carbonate → 3-iodo-4-methyl-N-(3-pyridin-2-yl-phenyl)benzamide

HRID 889325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889325
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.[NH2:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>S(Cl)(Cl)=O>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:14]=1)=[O:7]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 4595173-(2-Pyridyl)anilineHCID 6216403-Iodo-4-methylbenzoic acid

Produkt 1

HCID 219145303-iodo-4-methyl-N-(3-pyridin-2-yl-phenyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

3-Iodo-4-methylbenzoic acid (154 mg, 0.59 mmol) was heated at 80° C. in thionyl chloride (2 ml) for 3 hrs. The reaction was allowed to cool to room temperature and the excess thionyl chloride evaporated under vacuum. The residue was dissolved in acetone (3 ml), 2-(3-aminophenyl)pyridine (100 mg, 0.59 mmol) and sodium carbonate (400 mg) were added to the solution. The reaction was stirred at room temperature for 11 days, filtered and the filtrate reduced to dryness under vacuum. The residue was dissolved in ether and filtered through a bond-elut (1 g, silica), washing with ether. The solvent was evaporated from the combined filtrate and washings to give 3-iodo-4-methyl-N-(3-pyridin-2-yl-phenyl)benzamide as a cream foam. NMR: δH CDCl3 8.70,(1H, dt), 8.33,(1H, d), 8.18,(1H, t), 7.93-7.89,(2H, m), 7.79-7.75,(4H, m), 7.50,(1H, t), 7.35,(1H, d), 7.26,(1H, m), 2.51,(3H, s).

Aufarbeitung

  1. customthe excess thionyl chloride evaporated under vacuum
  2. dissolutionThe residue was dissolved in acetone (3 ml)
  3. filtrationfiltered
  4. dissolutionThe residue was dissolved in ether
  5. filtrationfiltered through a bond-elut (1 g, silica)
  6. washwashing with ether
  7. customThe solvent was evaporated from the combined filtrate and washings

Quellen und Nachweise

ORD-Eintrag
ord-c37544445416404393401f58cdedc28b
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252818B2

Notizen zur Reaktion

Wird geladen…