m-Aminoacetanilide → N-(3-{[(7-{[(3-Hydroxyphenyl)amino]sulfonyl}-9-oxo-9H-fluoren-2-yl)sulfonyl]amino}phenyl)acetamide

HRID 2120916Notes

Reaction equation

HRID 2120916 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[NH2:9][C:10]1[CH:11]=[C:12]([NH:16][C:17](=[O:19])[CH3:18])[CH:13]=[CH:14][CH:15]=1.[O:20]=[C:21]1[C:33]2[CH:32]=[C:31]([S:34](Cl)(=[O:36])=[O:35])[CH:30]=[CH:29][C:28]=2[C:27]2[C:22]1=[CH:23][C:24]([S:38](Cl)(=[O:40])=[O:39])=[CH:25][CH:26]=2>N1C=CC=CC=1>[OH:8][C:4]1[CH:3]=[C:2]([NH:1][S:34]([C:31]2[CH:32]=[C:33]3[C:28]([C:27]4[CH:26]=[CH:25][C:24]([S:38]([NH:9][C:10]5[CH:11]=[C:12]([NH:16][C:17](=[O:19])[CH3:18])[CH:13]=[CH:14][CH:15]=5)(=[O:39])=[O:40])=[CH:23][C:22]=4[C:21]3=[O:20])=[CH:29][CH:30]=2)(=[O:35])=[O:36])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7604m-AminoacetanilideHCID 115683-AminophenolHCID 27945729-Oxo-9H-fluorene-2,7-disulfonyl dichloride

Product 1

HCID 9985345N-(3-{[(7-{[(3-Hydroxyphenyl)amino]sulfonyl}-9-oxo-9H-fluoren-2-yl)sulfonyl]amino}phenyl)acetamideYield 39%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Aminophenol (0.29 g, 2.65 mmmol) and N-(3-aminophenyl)acetamide (0.49 g, 2.65 mmol) in pyridine were treated with 9-oxo-9H-fluorene-2,7-disulfonyl dichloride (1.00 g, 2.65 mmol) in one portion at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 1 hour after which the volatiles were evaporated under reduced pressure. The residue was partitioned between ethyl acetate and H2O. The separated organic phase was washed with 1N HCl, brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (85% ethyl acetate/hexanes) to provide the title compound as a yellow solid (577 mg, 39% yield). 1H NMR (300 MHz, DMSO-d6) δ 9.91 (bs, 1H), 9.47 (s, 1H), 7.9-8.1 (m, 6H), 7.48 (m, 1H), 7.26 bd, 1H), 7.12 (t, 1H), 6.99 (t, 1H), 6.75 (m, 1H), 6.58 (t, 1H), 6.52 (dd, 1H), 6.42 (dd, 1H), 1.98 (s, 3H); MS (ESI) 562 (M−H)−.

Workup

  1. customwere evaporated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and H2O
  3. washThe separated organic phase was washed with 1N HCl, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (85% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-3e2601917769433cb56db3d368e6f642
Source dataset
uspto-grants-2004_02
Patent number
US06693136B1

Reaction notes

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