4-Trifluoromethyl-1,2-phenylenediamine → HCID 11646459, compound

HRID 1497483Notes

Reaction equation

HRID 1497483 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2[CH:16]=[CH:15][C:11]([C:12](O)=O)=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[F:17][C:18]([F:28])([F:27])[C:19]1[CH:20]=[C:21]([NH2:26])[C:22]([NH2:25])=[CH:23][CH:24]=1>O=P(Cl)(Cl)Cl.O>[Cl:1][C:2]1[C:3]([C:8]2[CH:16]=[CH:15][C:11]([C:12]3[NH:26][C:21]4[CH:20]=[C:19]([C:18]([F:17])([F:27])[F:28])[CH:24]=[CH:23][C:22]=4[N:25]=3)=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 5208224-Trifluoromethyl-1,2-phenylenediamineHCID 221704544-(3-Chloropyridin-2-yl)benzoic acid

Product 1

HCID 11646459HCID 11646459, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24813Phosphorus oxychlorideSolvent

Procedure

To a solution of 0.64 g (2.75 mmol) 4-(3-chloropyridin-2-yl)benzoic acid in 20 mL POCl3 was added 0.44 g (2.5 mmol) 4-trifluoromethylbenzene-1,2-diamine, followed by stirring for 3 hours in a heat flux condition. The solution was cooled to room temperature and dissolved in distilled water. After the adjustment of pH to 8-10 with ammonia, extraction was conducted using ethyl acetate. The organic layer was dried over magnesium sulfate and vacuum concentrated. The residue thus obtained was separated using column chromatography (developing solvent: chloroform/methanol=30/1) to produce 0.61 g of 2-[4-(3-chloropyridin-2-yl)phenyl]-6-trifluoromethyl-1H-benzoimidazole (yield 65%).

Workup

  1. extractionAfter the adjustment of pH to 8-10 with ammonia, extraction
  2. dry with materialThe organic layer was dried over magnesium sulfate and vacuum
  3. concentrationconcentrated
  4. customThe residue thus obtained
  5. customwas separated

Sources & evidence

ORD record
ord-f3029dcd277d4aa5a8adf9da224cf855
Source dataset
uspto-grants-2015_12
Patent number
US09199965B2

Reaction notes

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