Bromine → N-[4-[4-(4-Methoxyphenyl)-2-methyl-1,3-thiazol-5-YL]-2-pyridyl]benzamide

HRID 2212353ノート

反応式

HRID 2212353 の反応式
BrBr.[C:3]([NH:11][C:12]1[CH:17]=[C:16]([CH2:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=O)[CH:15]=[CH:14][N:13]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:29]([NH2:32])(=[S:31])[CH3:30].C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]2[N:32]=[C:29]([CH3:30])[S:31][C:18]=2[C:16]2[CH:15]=[CH:14][N:13]=[C:12]([NH:11][C:3](=[O:10])[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:17]=2)=[CH:22][CH:23]=1

参加物

6

反応物 4

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 2723949ThioacetamideHCID 219642602-(2-Benzoylamino-4-pyridyl)-1-(4-methoxyphenyl)ethanone

生成物 1

HCID 10135691N-[4-[4-(4-Methoxyphenyl)-2-methyl-1,3-thiazol-5-YL]-2-pyridyl]benzamide収率 50%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Bromine (0.18 mL, 3.5 mmol) was added to a solution of 2-(2-benzoylamino-4-pyridyl)-1-(4-methoxyphenyl)ethanone (1.2 g, 3.4 mmol) in acetic acid (10 mL) and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated. The residue was dissolved in N,N-dimethylformamide (20 mL), thioacetamide (0.30 g, 19 mmol) was added to the solution and the mixture was stirred at room temperature for 20 hours. An aqueous saturated solution of sodium hydrogencarbonate (20 mL) was added to the reaction mixture, the resulting mixture was extracted with ethyl acetate and the extract was washed with water. The extract was dried and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, 1:1) to obtain 0.68 g (yield 50%) of the title compound.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in N,N-dimethylformamide (20 mL)
  3. stirringthe mixture was stirred at room temperature for 20 hours
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washthe extract was washed with water
  6. customThe extract was dried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 1:1)

出典と根拠

ORDレコード
ord-7f361e30365f42a1b6b7e91bdbb1d651
出典データセット
uspto-grants-2006_09
特許番号
US07101899B1

反応ノート

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