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

HRID 1246013Notes

Reaction equation

HRID 1246013 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3734366a48844362af754fbcee8bdb63
Source dataset
uspto-grants-2006_10
Patent number
US07125898B2

Reaction notes

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