3-Aminophenol → N,N'-bis(3-hydroxyphenyl)-9-oxo-9H-fluorene-2,7-disulfonamide

HRID 2120913Notes

Reaction equation

HRID 2120913 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[O:9]=[C:10]1[C:22]2[CH:21]=[C:20]([S:23](Cl)(=[O:25])=[O:24])[CH:19]=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][C:13]([S:27](Cl)(=[O:29])=[O:28])=[CH:14][CH:15]=2>N1C=CC=CC=1>[OH:8][C:4]1[CH:3]=[C:2]([NH:1][S:27]([C:13]2[CH:14]=[CH:15][C:16]3[C:17]4[C:22](=[CH:21][C:20]([S:23]([NH:1][C:2]5[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[CH:3]=5)(=[O:25])=[O:24])=[CH:19][CH:18]=4)[C:10](=[O:9])[C:11]=3[CH:12]=2)(=[O:29])=[O:28])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 115683-AminophenolHCID 27945729-Oxo-9H-fluorene-2,7-disulfonyl dichloride

Product 1

HCID 10075434N,N'-bis(3-hydroxyphenyl)-9-oxo-9H-fluorene-2,7-disulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Aminophenol (0.91 g, 8.38 mmol) in pyridine was treated with 9-oxo-9H-fluorene-2,7-disulfonyl dichloride (1.58 g, 4.19 mmol, purchased from Maybridge) in one portion at 0° C. After two hours, the volatiles were removed at reduced pressure and the residue was partitioned between ethyl acetate and H2O. The organic layer was separated, washed with 1N HCl, brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (8% CH3OH/CH2Cl2) to provide the title compound as a yellow solid (1.97 g, 90% yield). 1H NMR (300 MHz, DMSO-d6) δ 10.31 (s, 2H), 9.50 (s, 2H), 7.97-8.11 (m, 4H), 7.92 (d, 2H), 7.0 (t, 2H), 6.49-6.64 (m, 4H), 6.43 (m, 2H); MS (DCI/NH3) 540 (M+NH4)+.

Workup

  1. customthe volatiles were removed at reduced pressure
  2. customthe residue was partitioned between ethyl acetate and H2O
  3. customThe organic layer was separated
  4. washwashed with 1N HCl, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (8% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-52870c9ce28d44028726b5df09427619
Source dataset
uspto-grants-2004_02
Patent number
US06693136B1

Reaction notes

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