Ethylenediamine → Dansylethylenediamine

HRID 846833Notes

Reaction equation

HRID 846833 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[S:5](Cl)([C:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:13]([N:14]([CH3:16])[CH3:15])[C:12]=2[CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6].[OH-].[Na+]>C(Cl)(Cl)Cl>[S:5]([NH:3][CH2:2][CH2:1][NH2:4])([C:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:13]([N:14]([CH3:16])[CH3:15])[C:12]=2[CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 11801Dansyl chloride2×HCID 14798Sodium Hydroxide

Product 1

HCID 161851DansylethylenediamineYield 39.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of ethylenediamine (635 mg, 10.6 mmol) in chloroform (10 ml), a solution of dansyl chloride (285 mg, 1.06 mmol) in chloroform (12 ml) was dropwise added, and the reaction mixture was stirred at room temperature overnight, followed by addition of a bit of 1 N sodium hydroxide thereto for hydrolysis of unreacted dansyl chloride. The reaction mixture was concentrated, and the residue was combined with acetone. Insoluble materials were removed by filtration, and the filtrate was concentrated. Water (50 ml) was added to the residue, and extracted with ethyl acetate three times. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was dissolved in a small amount of ethyl acetate, a bit of n-hexane was added thereto, and the resultant mixture was allowed to stand at room temperature overnight. The precipitate was collected and recrystallized from ethyl acetate to give Compound (1) (124 mg). Yield, 63 %.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customInsoluble materials were removed by filtration
  3. concentrationthe filtrate was concentrated
  4. additionWater (50 ml) was added to the residue
  5. extractionextracted with ethyl acetate three times
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in a small amount of ethyl acetate
  9. additiona bit of n-hexane was added
  10. waitto stand at room temperature overnight
  11. customThe precipitate was collected
  12. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1b420ae97958419bbcd575af33944adc
Source dataset
uspto-grants-1992_08
Patent number
US05138039

Reaction notes

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