Ethylenediamine → N-(2-Aminoethyl)naphthalene-1-sulfonamide

HRID 846836Notes

Reaction equation

HRID 846836 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].C(N(CC)CC)C.[C:12]1([S:22](Cl)(=[O:24])=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1>CN(C)C=O>[C:12]1([S:22]([NH:3][CH2:2][CH2:1][NH2:4])(=[O:24])=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 8471TriethylamineHCID 665601-Naphthalenesulfonyl chloride

Product 1

HCID 19773793N-(2-Aminoethyl)naphthalene-1-sulfonamideYield 3.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of ethylenediamine (1.06 g, 17.6 mmol) in dimethylformamide (10 ml), triethylamine (1.79 g, 17.7 mmol) was added, followed by stirring. With stirring at room temperature, a solution of 1-naphtalenesulfonyl chloride (4.00 g, 17.6 mmol) in dimethylformamide (15 ml) was dropwise added thereto, and the reaction was carried out in an ice bath for 1 hour. Insoluble materials were removed by filtration, and the filtrate was concentrated. To the residue, chloroform and water were added, and insoluble materials were filtered off. Furthermore, the aqueous layer was separated, washed with ethyl acetate twice and adjusted to pH 11 with potassium carbonate, followed by extraction with ethyl acetate three times. The extracts were collected, washed with water twice, dried over anhydrous sodium sulfate and concentrated. The residue was allowed to stand in a refrigerator overnight, and the precipitate was collected and recrystallized from ethyl acetate to give Compound (10) (153 mg). Yield, 4%.

Workup

  1. stirringWith stirring at room temperature
  2. customInsoluble materials were removed by filtration
  3. concentrationthe filtrate was concentrated
  4. additionTo the residue, chloroform and water were added
  5. filtrationinsoluble materials were filtered off
  6. customFurthermore, the aqueous layer was separated
  7. washwashed with ethyl acetate twice
  8. extractionfollowed by extraction with ethyl acetate three times
  9. customThe extracts were collected
  10. washwashed with water twice
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated
  13. customto stand in a refrigerator overnight
  14. customthe precipitate was collected
  15. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-35f6b832034d4f52b80af277bdf053d2
Source dataset
uspto-grants-1992_08
Patent number
US05138039

Reaction notes

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