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

HRID 2108952ノート

反応式

HRID 2108952 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fdb2d2cec849437ebc4930f951bae2eb
出典データセット
uspto-grants-2009_04
特許番号
US07514456B2

反応ノート

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