Hydrochloric Acid → HCID 11646459, compound

HRID 1497481Notes

Reaction equation

HRID 1497481 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.Cl>N1C=CC=CC=1>[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5208224-Trifluoromethyl-1,2-phenylenediamineHCID 221704544-(3-Chloropyridin-2-yl)benzoic acid

Product 1

HCID 11646459HCID 11646459, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 0.58 g (2.5 mmol) 4-(3-chloropyridin-2-yl)benzoic acid in 30 mL anhydrous pyridine was added 0.44 g (2.5 mmol) 4-trifluoromethylbenzene-1,2-diamine, followed by stirring for 6 hours in a heat flux condition. After cooling to room temperature, cold water (100 mL) containing HCl (10 mL) was added to the solution, which was then allowed to stand for 30 min to form precipitates. These were separated using column chromatography (developing solvent: chloroform/methanol=30/1) to produce 0.70 g of 2-[4-(3-chloropyridin-2-yl)phenyl]-6-trifluoromethyl-1H-benzoimidazole (yield 75%).

Workup

  1. additionwas added to the solution, which
  2. waitto stand for 30 min
  3. customto form
  4. customprecipitates
  5. customThese were separated

Sources & evidence

ORD record
ord-8af74f4d135e46288943e134e031fe89
Source dataset
uspto-grants-2015_12
Patent number
US09199965B2

Reaction notes

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