Azobisisobutyronitrile → HCID 57656308, compound

HRID 2041450Notes

Reaction equation

HRID 2041450 reaction equation
[F:1][C:2]([F:16])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.C1C(=O)[N:21](Br)C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]([F:16])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][NH2:21])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 3278588HCID 3278588, compound

Product 1

HCID 57656308HCID 57656308, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

Combine 4-(difluoro-phenyl-methyl)-toluene (0.29 g, 1.35 mmol, prepared by following the procedure described in Tetrahedron 1996, 52, 9), NBS (0.26 g, 1.48 mmol), and AIBN (6 mg, 0.03 mmol) in carbon tetrachloride (8 mL) and heat at 80° C. for 16 h. Evaporate the mixture and pass the residue through a pad of silica gel washing with hexane and evaporate the filtrate. Dissolve the residue in methanol and add dropwise to 7M ammonia in methanol (100 mL) at 0° C. After 4.5 h, evaporate the mixture and isolate the amine by SCX chromatography (0.1 g, 32%). MS (ES+) m/z: 234 (M+H)+.

Workup

  1. customEvaporate the mixture
  2. customevaporate the filtrate
  3. dissolutionDissolve the residue in methanol
  4. additionadd dropwise to 7M ammonia in methanol (100 mL) at 0° C
  5. customevaporate the mixture

Sources & evidence

ORD record
ord-247beb8f8f7e4d139b1ebc1e4d6650ab
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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