Isocyanic acid, m-(fluorosulfonyl)phenyl ester → HCID 20312711, compound

HRID 2072332Notes

Reaction equation

HRID 2072332 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:33]([NH:35][C:36]2[CH:37]=[C:38]([S:54]([OH:57])(=[O:56])=[O:55])[CH:39]=[C:40]3[C:45]=2[C:44]([S:46]([OH:49])(=[O:48])=[O:47])=[CH:43][C:42]([S:50]([OH:53])(=[O:52])=[O:51])=[CH:41]3)=[O:34])[CH:5]=[C:6]([C:8]([NH:10][C:11]2[CH:12]=[C:13]([S:29]([OH:32])(=[O:31])=[O:30])[CH:14]=[C:15]3[C:20]=2[C:19]([S:21]([OH:24])(=[O:23])=[O:22])=[CH:18][C:17]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:16]3)=[O:9])[CH:7]=1.[F:58][S:59]([C:62]1[CH:63]=[C:64]([N:68]=[C:69]=[O:70])[CH:65]=[CH:66][CH:67]=1)(=[O:61])=[O:60]>O>[F:58][S:59]([C:62]1[CH:63]=[C:64]([NH:68][C:69](=[O:70])[NH:1][C:2]2[CH:3]=[C:4]([C:33]([NH:35][C:36]3[CH:37]=[C:38]([S:54]([OH:57])(=[O:56])=[O:55])[CH:39]=[C:40]4[C:45]=3[C:44]([S:46]([OH:49])(=[O:47])=[O:48])=[CH:43][C:42]([S:50]([OH:53])(=[O:52])=[O:51])=[CH:41]4)=[O:34])[CH:5]=[C:6]([C:8]([NH:10][C:11]3[CH:12]=[C:13]([S:29]([OH:32])(=[O:30])=[O:31])[CH:14]=[C:15]4[C:20]=3[C:19]([S:21]([OH:24])(=[O:22])=[O:23])=[CH:18][C:17]([S:25]([OH:28])(=[O:26])=[O:27])=[CH:16]4)=[O:9])[CH:7]=2)[CH:65]=[CH:66][CH:67]=1)(=[O:61])=[O:60]

Participants

4

Reactant 2

HCID 9819Isocyanic acid, m-(fluorosulfonyl)phenyl esterHCID 233351918,8'-[(5-Amino-m-phenylene)bis(carbonylimino)]di-1,3,6-naphthalenetrisulfonic acid

Product 1

HCID 20312711HCID 20312711, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of 3.0 g of 8,8'-[(5-amino-m-phenylene)bis(carbonylimino)]di-1,3,6-naphthalenetrisulfonic acid, hexasodium salt in 45 ml of water is added 3.0 g of m-fluorosulfonylphenylisocyanate. Stirring is continued for 6 hours at room temperature, the resulting mixture is heated to about 95° C and is filtered through diatomaceous earth. The filter pad is washed with 40 ml of hot water and the filtrate is diluted with 500 ml of anhydrous ethanol while heating in a steam bath. The solution is filtered after standing at room temperature for 72 hours and the precipitate is washed with absolute ethanol followed by ether to give 8,8'-{{5-{3-[m-(fluorosulfonyl)phenyl]ureido}-1,3-phenylene}bis(carbonylimino)}di-1,3,6-naphthalenetrisulfonic acid, hexasodium salt.

Workup

  1. filtrationis filtered through diatomaceous earth
  2. washThe filter pad is washed with 40 ml of hot water
  3. additionthe filtrate is diluted with 500 ml of anhydrous ethanol
  4. temperaturewhile heating in a steam bath
  5. filtrationThe solution is filtered
  6. waitafter standing at room temperature for 72 hours
  7. washthe precipitate is washed with absolute ethanol

Sources & evidence

ORD record
ord-f7730a2ee756486fb35f5b09a95bad5f
Source dataset
uspto-grants-1977_09
Patent number
US04051176

Reaction notes

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