Bis(2-chloroethyl)amine → 210992-98-6

HRID 1458989Notes

Reaction equation

HRID 1458989 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6]Cl.[F:8][C:9]1[CH:10]=[C:11]([CH:13]=[C:14]([F:16])[CH:15]=1)[NH2:12].C(=O)([O-])[O-].[K+].[K+]>C(O)CCC>[ClH:1].[F:8][C:9]1[CH:10]=[C:11]([N:12]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[CH:13]=[C:14]([F:16])[CH:15]=1

Participants

5

Reactant 3

HCID 9533Bis(2-chloroethyl)amineHCID 11430Potassium CarbonateHCID 965953,5-Difluoroaniline

Product 1

HCID 18520526210992-98-6Yield 69.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

13.7 g of bis-(2-chloroethyl)amine was suspended in 120 ml of butanol. To the obtained solution was added 10 g of 3,5-difluoroaniline and the mixture was heated under reflux for 48 hours. After cooling, 10.6 g of potassium carbonate was added and the obtained mixture was heated under reflux for additional 24 hours. Then crystals were collected by filtration, dissolved in water, extracted with chloroform, successively washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was dissolved in a small amount of chloroform and converted into hydrochloride by adding a 4N hydrochloric acid/dioxane solution. After filtration, 12.6 g of the title compound was obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 48 hours
  3. temperatureAfter cooling
  4. temperaturethe obtained mixture was heated
  5. temperatureunder reflux for additional 24 hours
  6. filtrationThen crystals were collected by filtration
  7. dissolutiondissolved in water
  8. extractionextracted with chloroform
  9. washsuccessively washed with water
  10. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  11. customAfter evaporating the solvent
  12. dissolutionthe residue was dissolved in a small amount of chloroform
  13. additionby adding a 4N hydrochloric acid/dioxane solution
  14. filtrationAfter filtration

Sources & evidence

ORD record
ord-e1d6739f0d7744d0b8ce39bf9078c717
Source dataset
uspto-grants-1998_12
Patent number
US05852019

Reaction notes

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