3-(Trifluoromethyl)phenyl isocyanate → HCID 20312707, compound

HRID 2072331Notes

Reaction equation

HRID 2072331 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][C:59]([F:70])([F:69])[C:60]1[CH:61]=[C:62]([N:66]=[C:67]=[O:68])[CH:63]=[CH:64][CH:65]=1>O>[F:58][C:59]([F:69])([F:70])[C:60]1[CH:65]=[CH:64][CH:63]=[C:62]([NH:66][C:67](=[O:68])[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:61]=1

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 233351918,8'-[(5-Amino-m-phenylene)bis(carbonylimino)]di-1,3,6-naphthalenetrisulfonic acid

Product 1

HCID 20312707HCID 20312707, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of 4.0 g of 8,8'-[(5-amino-1,3-phenylene)bis(carbonylimino)]di-1,3,6-naphthalenetrisulfonic acid, hexasodium salt in 50 ml of water is added 4.0 ml of 3-trifluoromethylphenyl isocyanate. Stirring is continued for 6 hours at room temperature then the resulting mixture is heated to 95° C, is filtered through diatomaceous earth and washed with 50 ml of hot water. The hot filtrate is salted with 55 g of sodium acetate trihydrate and after standing for 40 hours is diluted with 700 ml of anhydrous ethanol. The precipitate is filtered and washed with absolute ethanol and ether. The product is then boiled and triturated with 100 ml of absolute ethanol, cooled to room temperature and is filtered and washed with absolute ethanol followed by ether to give 8,8'-{{5-[3-(α,α,α-trifluoro-m-tolyl)ureido]-1,3-phenylene}bis(carbonylimino)}di-1,3,6-naphthalenetrisulfonic acid, hexasodium salt.

Workup

  1. filtrationis filtered through diatomaceous earth
  2. washwashed with 50 ml of hot water
  3. waitafter standing for 40 hours
  4. additionis diluted with 700 ml of anhydrous ethanol
  5. filtrationThe precipitate is filtered
  6. washwashed with absolute ethanol and ether
  7. customtriturated with 100 ml of absolute ethanol
  8. temperaturecooled to room temperature
  9. filtrationis filtered
  10. washwashed with absolute ethanol

Sources & evidence

ORD record
ord-d566d2dbff31480fb60c61e4001914f8
Source dataset
uspto-grants-1977_09
Patent number
US04051176

Reaction notes

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