Hydrochloric Acid → HCID 59445936, compound

HRID 1191571Notes

Reaction equation

HRID 1191571 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl([O-])(=O)=O.[K+].[I-:20].[K+].Cl>O.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([I:20])[CH:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 86754-Amino-4'-chlorodiphenylHCID 6426889Potassium Chlorate

Product 1

HCID 59445936HCID 59445936, compoundYield 89,208.797%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4′-chlorobiphenyl-4-ylamine (2.03 g, 0.01 mmol) in a mixed solvent system of methanol (10 ml) and distilled water (40 ml) is added potassium chlorate (0.830 g, 6.77 mmol) and potassium iodide (3.32 g, 0.02 mol). After heating the reaction mixture to 80° C., concentrated hydrochloric acid (0.60 ml) is added, and the mixture is further heated overnight at this temperature. The solution is cooled to room temperature and the crude product is extracted with diethyl ether (×3), followed by washing of the combined organic fractions with 5% aqueous sodium thiosulfate solution and distilled water. The organic phase is dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo to give a dark solid, which is triturated with hexanes to afford 4′-chloro-3-iodobiphenyl-4-ylamine (2.94 g) as light brown solid.

Workup

  1. temperaturethe mixture is further heated overnight at this temperature
  2. temperatureThe solution is cooled to room temperature
  3. extractionthe crude product is extracted with diethyl ether (×3)
  4. washby washing of the combined organic fractions with 5% aqueous sodium thiosulfate solution
  5. distillationdistilled water
  6. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate evaporated in vacuo
  9. customto give a dark solid, which
  10. customis triturated with hexanes

Sources & evidence

ORD record
ord-6904297700fc4a798aa00115c9858bba
Source dataset
uspto-grants-2014_03
Patent number
US08680012B2

Reaction notes

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