Azobisisobutyronitrile → HCID 57656308, compound

HRID 911583Notes

Reaction equation

HRID 911583 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-d6a1147406a94467b0bb2431df182585
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…