Azobisisobutyronitrile → HCID 22647970, compound

HRID 394172Notes

Reaction equation

HRID 394172 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH2:9][C:10]([NH:12][C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])=[O:11])=[C:6]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[F:28])[N:5]=[C:4]([S:29][CH3:30])[N:3]=1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Cl:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([Cl:19])[C:13]=1[N:12]1[C:2]2[N:3]=[C:4]([S:29][CH3:30])[N:5]=[C:6]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[F:28])[C:7]=2[CH:8]=[CH:9][C:10]1=[O:11]

Participants

4

Reactant 2

HCID 6547AzobisisobutyronitrileHCID 22647920HCID 22647920, compound

Product 1

HCID 22647970HCID 22647970, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a refluxing solution of 3-[4-chloro-6-(2,4-difluorophenyl)-2-(methylthio)pyrimidin-5-yl]-N-(2,6-dichlorophenyl)propanamide (0.06 g) and AIBN (0.005 g) in 8 mL of CCl4 was added recrystallized N-bromosuccinimide (0.026 g). The reaction was refluxed for 1 h, then removed from the heat. DBU (0.02 mL) was added and the solution was stirred at rt for 15 min. The reaction mixture was washed with 20 mL of saturated sodium bicarbonate and back extracted with 20 mL of CH2Cl2. The organic layer was washed with 20 mL of brine, dried with sodium sulfate, and concentrated to give the desired product. Mass spectrum m/z (ESI) 450.4 (M+1).

Workup

  1. customrecrystallized N-bromosuccinimide (0.026 g)
  2. temperatureThe reaction was refluxed for 1 h
  3. customremoved from the heat
  4. additionDBU (0.02 mL) was added
  5. washThe reaction mixture was washed with 20 mL of saturated sodium bicarbonate
  6. extractionback extracted with 20 mL of CH2Cl2
  7. washThe organic layer was washed with 20 mL of brine
  8. dry with materialdried with sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b17ca536c3a8421c9b456595047d020c
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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