3-Aminophenol → N,N'-bis(3-hydroxyphenyl)-9,10-dioxo-9,10-dihydro-2,7-anthracenedisulfonamide

HRID 2120921Notes

Reaction equation

HRID 2120921 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:23]2[CH:22]=[C:21]([S:24](Cl)(=[O:26])=[O:25])[CH:20]=[CH:19][C:18]=2[C:17](=[O:28])[C:16]2[C:11]1=[CH:12][C:13]([S:29](Cl)(=[O:31])=[O:30])=[CH:14][CH:15]=2>N1C=CC=CC=1.C(Cl)Cl>[OH:8][C:4]1[CH:3]=[C:2]([NH:1][S:29]([C:13]2[CH:14]=[CH:15][C:16]3[C:17](=[O:28])[C:18]4[C:23](=[CH:22][C:21]([S:24]([NH:1][C:2]5[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[CH:3]=5)(=[O:26])=[O:25])=[CH:20][CH:19]=4)[C:10](=[O:9])[C:11]=3[CH:12]=2)(=[O:31])=[O:30])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 115683-AminophenolHCID 234366039,10-Dioxo-9,10-dihydro-anthracene-2,7-disulfonyl dichloride

Product 1

HCID 10347522N,N'-bis(3-hydroxyphenyl)-9,10-dioxo-9,10-dihydro-2,7-anthracenedisulfonamideYield 28%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

3-aminophenol (0.76 g, 7 mmol) in pyridine (10 ml) was treated with the product from Example 10A in methylene chloride. The mixture was stirred at room temperature for 18 hours and the solvents removed under reduced pressure. The residue was taken up in ethyl acetate, washed three times with 1N hydrochloric acid, dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was filtered through a pad of silica gel with 5% methanol in methylene chloride. The filtrate was concentrated under reduced pressure and the residue was taken up in a mixture of ethyl acetate:hexanes (1:1). The mixture was washed three times with water, dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was titurated with methylene chloride and the orange solid collected by filtration to provide the title compound (0.47 g, 28% yield for 2 steps). 1H NMR (CD3OD) δ 7.16 (d, 2H, J=1.5 Hz), 6.86 (d, 2H, J=6 Hz), 6.69 (dd, 2H, J1=6 Hz, J2=1.5 Hz), 5.55-5.47 (m, 2H), 5.20-4.95 (m, 6H); MS (ESI−) 549 (M−H)−.

Workup

  1. customthe solvents removed under reduced pressure
  2. washwashed three times with 1N hydrochloric acid
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. filtrationThe residue was filtered through a pad of silica gel with 5% methanol in methylene chloride
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. additionthe residue was taken up in a mixture of ethyl acetate:hexanes (1:1)
  9. washThe mixture was washed three times with water
  10. dry with materialdried with magnesium sulfate
  11. filtrationfiltered
  12. concentrationthe filtrate concentrated under reduced pressure
  13. filtrationthe orange solid collected by filtration

Sources & evidence

ORD record
ord-a4acd6ae54834b16a7dd00dceab2e3f8
Source dataset
uspto-grants-2004_02
Patent number
US06693136B1

Reaction notes

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