HCID 12899707, compound → HCID 16161244, compound

HRID 2286473Notes

Reaction equation

HRID 2286473 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:26]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:27])[C:5]([C:17]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:18])=[C:6]([C:8]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])[CH:7]=1.[C:35]1([S:57](Cl)(=[O:59])=[O:58])[C:44]2[CH:43]=[C:42]([S:45](Cl)(=[O:47])=[O:46])[CH:41]=[C:40]([S:49](Cl)(=[O:51])=[O:50])[C:39]=2[CH:38]=[C:37]([S:53](Cl)(=[O:55])=[O:54])[CH:36]=1>N1C=CC=CC=1>[C:35]1([S:57]([NH:1][C:2]2[CH:7]=[C:6]([C:8]([O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:9])[C:5]([C:17]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:18])=[C:4]([C:26]([O:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:27])[CH:3]=2)(=[O:59])=[O:58])[C:44]2[C:39](=[C:40]([S:49]([NH:1][C:2]3[CH:7]=[C:6]([C:8]([O:10][C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)=[O:9])[C:5]([C:17]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:18])=[C:4]([C:26]([O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:27])[CH:3]=3)(=[O:51])=[O:50])[CH:41]=[C:42]([S:45]([NH:1][C:2]3[CH:7]=[C:6]([C:8]([O:10][C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)=[O:9])[C:5]([C:17]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:18])=[C:4]([C:26]([O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:27])[CH:3]=3)(=[O:47])=[O:46])[CH:43]=2)[CH:38]=[C:37]([S:53]([NH:1][C:2]2[CH:7]=[C:6]([C:8]([O:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[O:9])[C:5]([C:17]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:18])=[C:4]([C:26]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:27])[CH:3]=2)(=[O:55])=[O:54])[CH:36]=1

Participants

4

Reactant 2

HCID 12899707HCID 12899707, compoundHCID 12900263HCID 12900263, compound

Product 1

HCID 16161244HCID 16161244, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 36.27 g. of 5-amino-1,2,3-benzenetricarboxylic acid, triphenyl ester in 150 ml. of dry pyridine is added 12.0 g. of 1,3,5,7-naphthalenetetrasulfonyl chloride and the mixture is stirred at room temperature for one hour and then at 55°-75° C. for 2 hours. The solution is poured into 840 ml. of 2 N hydrochloric acid and the resulting mixture is extracted with methylene chloride. The aqueous phase is filtered to remove the suspended solid which is washed with water and methylene chloride to provide 32.4 g. of a cream powder. The product is crystallized from acetone-methylene chloride and is then refluxed in acetonitrile:methanol (2:1) solution. The product is filtered and the filtrate cooled to 5° C. to provide additional product. The combined fractions are dried overnight in an Abderhalden apparatus at 110° C. to give 21.45 g. of beige powder, mp. >300° C.

Workup

  1. additionThe solution is poured into 840 ml
  2. extractionof 2 N hydrochloric acid and the resulting mixture is extracted with methylene chloride
  3. filtrationThe aqueous phase is filtered
  4. customto remove the suspended solid which
  5. washis washed with water and methylene chloride
  6. customto provide 32.4 g
  7. customThe product is crystallized from acetone-methylene chloride
  8. temperatureis then refluxed in acetonitrile:methanol (2:1) solution
  9. filtrationThe product is filtered
  10. customto provide additional product
  11. customThe combined fractions are dried overnight in an Abderhalden apparatus at 110° C.
  12. customto give 21.45 g

Sources & evidence

ORD record
ord-d7cdbe77ddd84ec1b8ebbd7e3aaa87c0
Source dataset
uspto-grants-1981_05
Patent number
US04266077

Reaction notes

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