2-Naphthalenecarboxaldehyde → N-[6{(Naphthalen-2-ylmethyl)-amino}-hexyl]-2-nitrobenzenesulfonamide

HRID 322480Notes

Reaction equation

HRID 322480 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11].[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[CH:32]=O>C1(C)C=CC=CC=1>[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[CH2:32][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:11])=[O:12]

Participants

4

Reactant 2

HCID 62012-NaphthalenecarboxaldehydeHCID 22719658N-(6-Aminohexyl)-2-nitrobenzene-1-sulfonamide--hydrogen chloride (1/1)

Product 1

HCID 12042301N-[6{(Naphthalen-2-ylmethyl)-amino}-hexyl]-2-nitrobenzenesulfonamideYield 37%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N-(6-Aminohexyl)-2-nitrobenzenesulfonamide hydrochloride (0.67 g, 2.0 mmol) and 2-naphthaldehyde (0.32 g, 2.1 mmol) in 75 mL of toluene was refluxed using a Dean Stark trap for 20 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in ethanol (40 mL) and sodium borohyride (0.020 g, 6.0 mmol) was added. After the reaction was complete (6 h), the solvent was evaporated and residue taken up in 30 mL of saturated sodium chloride solution and extracted with ethyl acetate (3×40 mL), washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated to afford an oil. The oil was flash chromatographed over silica gel to afford the titled compound (0.16 g, 37%) which was converted into hydrochloride salt (mp 169° C.).

Workup

  1. temperaturewas refluxed
  2. customfor 20 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethanol (40 mL)
  5. additionsodium borohyride (0.020 g, 6.0 mmol) was added
  6. custom(6 h)
  7. customthe solvent was evaporated
  8. extractionextracted with ethyl acetate (3×40 mL)
  9. washwashed with saturated sodium chloride solution
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated
  12. customto afford an oil
  13. customchromatographed over silica gel

Sources & evidence

ORD record
ord-c7001f52dbcb45c29b63eeee31190511
Source dataset
uspto-grants-2001_04
Patent number
US06211241B1

Reaction notes

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