Azobisisobutyronitrile → HCID 15457079, compound

HRID 1385945Notes

Reaction equation

HRID 1385945 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][C:8]([CH3:11])=[CH:7][C:6]=2[C:5]([C:12]2[C:13](=[O:23])[N:14]([CH3:22])[C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)=[C:4]([F:24])[CH:3]=1.C1C(=O)N([Br:32])C(=O)C1.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:32][CH2:11][C:8]1[O:9][C:10]2[C:2]([Cl:1])=[CH:3][C:4]([F:24])=[C:5]([C:12]3[C:13](=[O:23])[N:14]([CH3:22])[C:15]([C:18]([F:19])([F:21])[F:20])=[CH:16][CH:17]=3)[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 15457083HCID 15457083, compound

Product 1

HCID 15457079HCID 15457079, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

0.98 g (2.72 mmol) of 3-(7-chloro-5-fluoro-2-methylbenzofuran-4-yl)-1-methyl-6-trifluoromethyl-2-(1H)-pyridone was dissolved in 25 ml of carbon tetrachloride, and 0.51 g (2.86 mmol) of NBS and 0.04 g (0.27 mmol) of 2,2′-azobisisobutyronitrile were added thereto, followed by refluxing for 2 hours. Succinic acid imide was removed by filtration. Then, carbon tetrachloride was distilled off under reduced pressure, and the obtained residue was poured into water and extracted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and the obtained crude crystals were washed with n-hexane to obtain 0.94 g (yield: 79%) of the desired product. Melting point: 142-144° C. 1H-NMR (300 MHz, CDCl3) δ value: 3.73(3H,s), 4.56(2H,s), 6.66(1H,s), 6.80(1H,d), 7.20(1H,d), 7.55(1H,d)ppm.

Workup

  1. temperatureby refluxing for 2 hours
  2. customSuccinic acid imide was removed by filtration
  3. distillationThen, carbon tetrachloride was distilled off under reduced pressure
  4. additionthe obtained residue was poured into water
  5. extractionextracted with ethyl acetate
  6. washAfter washing with water
  7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  8. distillationEthyl acetate was distilled off under reduced pressure
  9. customthe obtained crude crystals
  10. washwere washed with n-hexane

Sources & evidence

ORD record
ord-6fc4bdbe5ac9490693b744e57027f24b
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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