2-Naphthalenesulfonyl chloride → HCID 9906236, compound

HRID 1815451Notes

Reaction equation

HRID 1815451 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][CH2:9][CH2:10][N:11]2C(=O)C3=CC=CC=C3C2=O)[CH2:3]1.O.NN.C(N(CC)CC)C.[CH:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][C:33]=1[S:42](Cl)(=[O:44])=[O:43]>C(O)C>[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][CH2:9][CH2:10][NH:11][S:42]([C:33]2[CH:34]=[CH:35][C:36]3[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:32]=2)(=[O:44])=[O:43])[CH2:3]1

Participants

6

Reactant 4

HCID 71252-Naphthalenesulfonyl chlorideHCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 22500572HCID 22500572, compound

Product 1

HCID 9906236HCID 9906236, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of the product of step c (437 mg, 1.53 mmol) in ethanol (10 ml) was added hydrazine hydrate (0.37 ml) and the reaction heated at reflux for 1.5 h. The resultant suspension was filtered, the filter-cake was washed with further ethanol (20 ml) and the filtrate was evaporated. The residue was suspended in DCM (20 ml) and the solid was removed by filtration. The filtrate was evaporated at reduced pressure and the residue was dissolved in DCM (5 ml). The solution was treated sequentially, with ice-cooling, with triethylamine (0.290 ml, 2.08 mmol) and 2-naphthalenesulfonyl chloride (217 mg, 1.39 mmol). The coolant was removed and the reaction mixture stirred at ambient temperature for 2 h. The reaction was diluted with DCM (20 ml), washed with water (20 ml) and brine (20 ml), and dried over anhydrous sodium sulfate. The filtrate was evaporated at reduced pressure and the residue was purified by flash column chromatography (90:10:1 DCM:methanol:ammonia) to afford the title compound (240 mg, 45%). 1H NMR 8.44 (1H, d, 1.2), 7.99-7.59 (6H, m), 2.98 (2H, t, 6.9), 2.76-2.69 (2H, m), 2.24 (3H, s), 1.87-1.84 (3H, m), 1.64-1.46 (5H, m), 1.21-1.13 (2H, m), 0.75 (1H, m). Microanalysis found C 64.32 H 7.75 N 7.59. C19H26N2O2S-0.5H2O requires C 64.19 H 7.76 N 7.88.

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 1.5 h
  3. filtrationThe resultant suspension was filtered
  4. washthe filter-cake was washed with further ethanol (20 ml)
  5. customthe filtrate was evaporated
  6. customthe solid was removed by filtration
  7. customThe filtrate was evaporated at reduced pressure
  8. dissolutionthe residue was dissolved in DCM (5 ml)
  9. additionThe solution was treated sequentially, with ice-
  10. customThe coolant was removed
  11. additionThe reaction was diluted with DCM (20 ml)
  12. washwashed with water (20 ml) and brine (20 ml)
  13. dry with materialdried over anhydrous sodium sulfate
  14. customThe filtrate was evaporated at reduced pressure
  15. customthe residue was purified by flash column chromatography (90:10:1 DCM:methanol:ammonia)

Sources & evidence

ORD record
ord-0488c2af7b694563b405cddbc5b69f14
Source dataset
uspto-grants-2005_04
Patent number
US06878736B1

Reaction notes

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