Potassium Carbonate → HCID 21938673, compound

HRID 382500Notes

Reaction equation

HRID 382500 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[C:11]=1[NH2:12].C(=O)([O-])[O-].[K+].[K+]>C1(C)C(C)=CC=CC=1.CCCCCCC.[Cu]>[Cl:9][C:10]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[C:11]=1[NH:12][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 122074-IodotolueneHCID 27340832-Chloro-4,6-difluoroaniline

Product 1

HCID 21938673HCID 21938673, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 7237O-XyleneSolventHCID 8900HeptaneSolvent

Procedure

A mixture of 4-iodotoluene (210 g, 0.96 mol), 2-chloro-4,6-difluoroaniline (204 g, 1.25 mol), copper powder (36 g, 0.57 mol), cuprous iodide (130 g, 0.68 mol), and potassium carbonate (118 g, 0.86 mol) in 500 ml of xylene is stirred vigorously and heated to reflux in a flask fitted with a Dean-Stark trap for 26 hours. After cooling to room temperature, the solids are filtered off, and the filter cake is washed with 100 ml of xylene. The solvents are evaporated under reduced pressure to give an oil which is dissolved in a mixture of 50 g of silica gel in 750 ml of heptane. The solids are filtered off and the solvents are evaporated under reduced pressure to give N-(2′-chloro-4′,6′-difluorophenyl)-4-methylaniline as an oil.

Workup

  1. temperatureheated
  2. temperatureto reflux in a flask
  3. customfitted with a Dean-Stark trap for 26 hours
  4. filtrationthe solids are filtered off
  5. washthe filter cake is washed with 100 ml of xylene
  6. customThe solvents are evaporated under reduced pressure
  7. customto give an oil which
  8. filtrationThe solids are filtered off
  9. customthe solvents are evaporated under reduced pressure

Sources & evidence

ORD record
ord-f36873b89aac4a73bec3ecf9ab6dd02d
Source dataset
uspto-grants-2001_10
Patent number
US06310099B1

Reaction notes

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