2-Naphthalenesulfonyl chloride → HCID 66818407, compound

HRID 1024708Notes

Reaction equation

HRID 1024708 reaction equation
[C:1]([C:3]1[CH:25]=[CH:24][C:6]([O:7][C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=3)[CH:11]=[CH:10][C:9]=2[NH2:23])=[CH:5][CH:4]=1)#[N:2].[CH:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][C:27]=1[S:36](Cl)(=[O:38])=[O:37].C(N(CC)C(C)C)(C)C>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:25]=[CH:24][C:6]([O:7][C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=3)[CH:11]=[CH:10][C:9]=2[NH:23][S:36]([C:27]2[CH:28]=[CH:29][C:30]3[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:26]=2)(=[O:38])=[O:37])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66820986HCID 66820986, compound

Product 1

HCID 66818407HCID 66818407, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,5-Bis-(4-cyano-phenoxy)-2-aminobenzene 0.175 g (0.54 mmol), 2-naphthalene-sulfonyl chloride 0.148 g (0.65 mmol) and N,N-diisopropylethylamine (DIPEA) 0.85 g (0.65 mmol) were dissolved in 5 ml of dry toluene and refluxed for 8 h. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between water and ethyl acetate after the pH was adjusted to 2 with 6 N HCl. The organic phase was washed with 1 M Na2CO3 (5×100 ml) and saturated brine solution. The solution was dried over sodium sulphate and concentrated to afford an oily residue, which was purified by column chromatography using hexane-ethyl acetate (10:2) to afford 0.190 g of the required product. 1H NMR (DMSO-d6): δ 6.45 (3H, m), 7.16 (5H, m), 7.42 (6H, m), 7.75 (2H, dd), 8.10 (2H, d), 8.35 (1H, s).

Workup

  1. temperaturerefluxed for 8 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was partitioned between water and ethyl acetate after the pH
  4. washThe organic phase was washed with 1 M Na2CO3 (5×100 ml) and saturated brine solution
  5. dry with materialThe solution was dried over sodium sulphate
  6. concentrationconcentrated
  7. customto afford an oily residue, which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-172b0c40d99744d1a9eb791869650ad7
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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