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

HRID 2212353Notes

Reaction equation

HRID 2212353 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-7f361e30365f42a1b6b7e91bdbb1d651
Source dataset
uspto-grants-2006_09
Patent number
US07101899B1

Reaction notes

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