Sodium Bicarbonate → HCID 11646459, compound

HRID 1497482Notes

Reaction equation

HRID 1497482 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.C([O-])(O)=O.[Na+]>Cl>[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 3

HCID 516892Sodium BicarbonateHCID 5208224-Trifluoromethyl-1,2-phenylenediamineHCID 221704544-(3-Chloropyridin-2-yl)benzoic acid

Product 1

HCID 11646459HCID 11646459, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of 0.64 g (2.75 mmol) 4-(3-chloropyridin-2-yl)benzoic acid in 25 mL 4N HCl was added 0.44 g (2.5 mmol) 4-trifluoromethylbenzene-1,2-diamine, followed by stirring at 180° C. for 6 hours. The solution was cooled to room temperature before the addition of 10% NaHCO3 (10 mL) and then extraction with 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. extractionextraction with ethyl acetate
  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-5127fb85a9434f9999dccba771952257
Source dataset
uspto-grants-2015_12
Patent number
US09199965B2

Reaction notes

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