Diaminostilbenedisulfonic acid → 2,2'-[(E)-1,2-Ethenediyl]bis(5-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}benzenesulfonic Acid)

HRID 277579

Reaction equation

HRID 277579 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:21]([OH:24])(=[O:23])=[O:22])[C:5]([CH:8]=[CH:9][C:10]2[C:11]([S:17]([OH:20])(=[O:19])=[O:18])=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=2)=[CH:6][CH:7]=1.[C:25](=[O:28])([O-:27])[O-].[Na+].[Na+].Cl[C:32]([O:34][CH2:35][CH:36]1[C:48]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[C:42]2[C:37]1=[CH:38][CH:39]=[CH:40][CH:41]=2)=[O:33]>O.O1CCOCC1>[CH:8](/[C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:32]([O:34][CH2:35][CH:36]2[C:48]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[C:42]3[C:37]2=[CH:38][CH:39]=[CH:40][CH:41]=3)=[O:33])=[CH:3][C:4]=1[S:21]([OH:24])(=[O:23])=[O:22])=[CH:9]\[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:25]([O:27][CH2:35][CH:36]2[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:42]=3[C:43]3[C:48]2=[CH:47][CH:46]=[CH:45][CH:44]=3)=[O:28])=[CH:12][C:11]=1[S:17]([OH:20])(=[O:19])=[O:18]

Participants

6

Reactant 3

HCID 6668Diaminostilbenedisulfonic acidHCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformate

Product 1

HCID 98539532,2'-[(E)-1,2-Ethenediyl]bis(5-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}benzenesulfonic Acid)Yield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of commercially available 4,4′-diaminostilbene-2,2′-disulfonic acid (10 g, 27.0 mmol) in a mixture of 270 mL water and 30 mL dioxane was added 14.3 g (135 mmol) of sodium carbonate and the solution stirred until homogeneous. At this time 9-fluorenylmethyl chloroformate was added and the mixture allowed to stir overnight. The solution was filtered and the solids washed with water (200 mL). The collected solids were then suspended in 600 mL of water and 50 mL conc hydrochloric acid added. After 30 minutes the solution was filtered and the solids dried in a vacuum oven overnight at 50° C. to provide the title compound 21.8 g (72%) as a orange-brown solid. MS (ES-NEG): [M−H] 813.

Workup

  1. stirringto stir overnight
  2. filtrationThe solution was filtered
  3. washthe solids washed with water (200 mL)
  4. addition50 mL conc hydrochloric acid added
  5. filtrationAfter 30 minutes the solution was filtered
  6. customthe solids dried in a vacuum oven overnight at 50° C.

Sources & evidence

ORD record
ord-d40d32ac680c4870a1bdaa82af14a527
Source dataset
uspto-grants-2002_03
Patent number
US06355633B1

Linked notes

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