Potassium Carbonate → HCID 11357080, compound

HRID 564871Notes

Reaction equation

HRID 564871 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].Cl.Cl[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)CCC>[F:1][C:2]1[CH:3]=[C:4]([N:5]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 27359133-Amino-5-fluorobenzotrifluoride

Product 1

HCID 11357080HCID 11357080, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To 60 ml of n-butanol were added 5.0 g of 3-fluoro-5-(trifluoromethyl)aniline and 5.0 g of bis(2-chloroethyl)amine hydrochloride, and the mixture was heated under reflux for 47 hours. To the reaction mixture was added 3.85 g of potassium carbonate, followed by heating under reflux for 24 hours. After cooling to room temperature, the solvent was removed by evaporation. The residue was dissolved in an 1N sodium hydroxide aqueous solution and extracted with chloroform-methanol (19:1 by volume). The extract was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was removed by evaporation, and the residue was subjected to silica gel column chromatography using a 9:1 (by volume) mixed solvent of chloroform and methanol as a developing solvent. The fraction containing the desired compound was concentrated to yield 2.1 g of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 47 hours
  3. temperatureby heating
  4. temperatureunder reflux for 24 hours
  5. customthe solvent was removed by evaporation
  6. dissolutionThe residue was dissolved in an 1N sodium hydroxide aqueous solution
  7. extractionextracted with chloroform-methanol (19:1 by volume)
  8. washThe extract was washed with a saturated sodium chloride aqueous solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was removed by evaporation
  11. additionmixed solvent of chloroform and methanol as a developing solvent
  12. additionThe fraction containing the desired compound
  13. concentrationwas concentrated

Sources & evidence

ORD record
ord-020d4de1438543f0bc722dca6ebfbab8
Source dataset
uspto-grants-2001_01
Patent number
US06169086A

Reaction notes

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