Dansyl chloride → N-(6-Aminohexyl)-5-(dimethylamino)naphthalene-1-sulfonamide

HRID 846834Notes

Reaction equation

HRID 846834 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].[S:9](Cl)([C:12]1[C:24]2[CH:23]=[CH:22][CH:21]=[C:17]([N:18]([CH3:20])[CH3:19])[C:16]=2[CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10]>CN(C)C=O>[S:9]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH2:8])([C:12]1[C:24]2[CH:23]=[CH:22][CH:21]=[C:17]([N:18]([CH3:20])[CH3:19])[C:16]=2[CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 11801Dansyl chlorideHCID 16402Hexamethylenediamine

Product 1

HCID 193720N-(6-Aminohexyl)-5-(dimethylamino)naphthalene-1-sulfonamideYield 34.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Hexamethylenediamine (5.39 g, 45.9 mmol) was combined with dimethylformamide (15 ml), and a solution of dansyl chloride (2.40 g, 8.7 mmol) in dimethylformamide (10 ml) was dropwise added thereto, followed by stirring at room temperature for 4 hours. Insoluble materials were removed by filtration, and the filtrate was stirred at room temperature overnight. After concentration, water and ethyl acetate were added to thereto, and 1 N hydrochloric acid was added thereto to adjust the aqueous layer to pH 4. The aqueous layer was washed with ethyl acetate three times, adjusted to pH 11 with potassium carbonate and extracted with ethyl acetate twice. The extracts were collected, washed with water three times, dried over anhydrous sodium sulfate and concentrated to give Compound (4) (1.04 g) as an oil. Yield, 34%.

Workup

  1. customInsoluble materials were removed by filtration
  2. stirringthe filtrate was stirred at room temperature overnight
  3. concentrationAfter concentration, water and ethyl acetate
  4. additionwere added to thereto, and 1 N hydrochloric acid
  5. additionwas added
  6. washThe aqueous layer was washed with ethyl acetate three times
  7. extractionextracted with ethyl acetate twice
  8. customThe extracts were collected
  9. washwashed with water three times
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-fa885da436e94577a268f67977a1a370
Source dataset
uspto-grants-1992_08
Patent number
US05138039

Reaction notes

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