Phenyl isocyanate → 4,4′-Bis(3-phenylureido)-2,2′-stilbenedisulfonic acid disodium salt

HRID 1429312Notes

Reaction equation

HRID 1429312 reaction equation
[CH:1](/[C:14]1[C:19]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:18][C:17]([NH2:24])=[CH:16][CH:15]=1)=[CH:2]\[C:3]1[C:8]([S:9]([OH:12])(=[O:11])=[O:10])=[CH:7][C:6]([NH2:13])=[CH:5][CH:4]=1.[OH-:25].[Na+:26].[C:27]1([N:33]=[C:34]=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O>[CH:1](/[C:14]1[C:19]([S:20]([O-:23])(=[O:22])=[O:21])=[CH:18][C:17]([NH:24][C:34]([NH:33][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:25])=[CH:16][CH:15]=1)=[CH:2]\[C:3]1[C:8]([S:9]([O-:12])(=[O:11])=[O:10])=[CH:7][C:6]([NH:13][C:34]([NH:33][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:35])=[CH:5][CH:4]=1.[Na+:26].[Na+:26]

Participants

5

Reactant 3

HCID 7672Phenyl isocyanate2×HCID 14798Sodium HydroxideHCID 52843784,4'-Diamino-2,2'-stilbenedisulfonic acid, (E)-

Product 1

HCID 64514254,4′-Bis(3-phenylureido)-2,2′-stilbenedisulfonic acid disodium saltYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(E)-6,6′-(Ethene-1,2-diyl)bis(3-aminobenzenesulfonic acid) (18.5 g, 0.05 mol) was dissolved in water (800 ml) by adjusting to pH 7 with 2N sodium hydroxide. Phenyl isocyanate (11.9 g, 0.10 mol) was added over a period of 90 minutes then stirred overnight. Further phenyl isocyanate (0.6 g, 0.005 mol) was added with a second overnight stir. The resultant suspended solid was filtered off, re-suspended in acetone, filtered off and dried for 24 h at 40° C. to give the title compound as a beige solid (31.7 g, 78%); C28H22N4Na2O8S2 requires C, 51.5%, N, 8.6%. found C, 44.8%, N, 6.9%, sample strength determined as 80% based on N content.

Workup

  1. stirringstir
  2. filtrationwas filtered off
  3. filtrationfiltered off
  4. customdried for 24 h at 40° C.

Sources & evidence

ORD record
ord-994d310c52644fe9a4c4e858d455fc41
Source dataset
uspto-grants-2015_01
Patent number
US08940681B2

Reaction notes

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