Hydrochloric Acid → HCID 16161244, compound

HRID 1164326Notes

Reaction equation

HRID 1164326 reaction equation
[C:1]1([O:7][C:8]([C:10]2[CH:15]=[C:14]([NH2:16])[CH:13]=[C:12]([C:17]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:18])[C:11]=2[C:26]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:27])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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.[OH2:61].Cl>N1C=CC=CC=1.CC(C)=O>[C:35]1([S:57]([NH:16][C:14]2[CH:15]=[C:10]([C:8]([O:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:9])[C:11]([C:26]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:27])=[C:12]([C:17]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:18])[CH:13]=2)(=[O:59])=[O:58])[C:44]2[C:39](=[C:40]([S:49]([NH:16][C:14]3[CH:15]=[C:10]([C:8]([O:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[O:9])[C:11]([C:26]([O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:27])=[C:12]([C:17]([O:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[O:61])[CH:13]=3)(=[O:51])=[O:50])[CH:41]=[C:42]([S:45]([NH:16][C:14]3[CH:15]=[C:10]([C:8]([O:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[O:9])[C:11]([C:26]([O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:27])=[C:12]([C:17]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:18])[CH:13]=3)(=[O:47])=[O:46])[CH:43]=2)[CH:38]=[C:37]([S:53]([NH:16][C:14]2[CH:15]=[C:10]([C:8]([O:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:9])[C:11]([C:26]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:27])=[C:12]([C:17]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:18])[CH:13]=2)(=[O:55])=[O:54])[CH:36]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 12899707HCID 12899707, compoundHCID 12900263HCID 12900263, compound

Product 1

HCID 16161244HCID 16161244, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1049PyridineSolvent

Procedure

To a solution of 36.27 g of 5-amino-1,2,3-benzenetricarboxylic acid triphenyl ester in 150 ml of pyridine at room temperature is added 12.0 g of 1,3,5,7-naphthalenetetrasulfonyl chloride. The mixture is stirred at room temperature for one hour, heated at 55°-75° C. for 2 hours and then poured into a mixture of 700 ml of water and 140 ml of concentrated hydrochloric acid with vigorous stirring. The mixture is extracted with 500 ml of dichloromethane, filtered and the solid is washed with water and dichloromethane then dried giving 32.4 g of crude product. This product is dissolved in 150 ml of acetone, filtered through celite and diluted with 300 ml of dichloromethane. The mixture is allowed to crystallize in a refrigerator. The solid is collected by filtration, washed with acetone:dichloromethane (1:2) and air dried. Two more crops are recovered by essentially the same procedure. The combined solids are refluxed in 200 ml of acetone, then in a mixture of 700 ml of acetonitrile and 350 ml of methanol. The solid is recovered by filtration and dried at 110° C. overnight giving 21.45 g of 5,5',5",5"'-[1,3,5,7-naphthalenetetrayltetrakis(sulfonylimino)]tetra-1,2,3-benzenetricarboxylic acid, dodecaphenyl ester.

Workup

  1. temperatureheated at 55°-75° C. for 2 hours
  2. extractionThe mixture is extracted with 500 ml of dichloromethane
  3. filtrationfiltered
  4. washthe solid is washed with water and dichloromethane
  5. customthen dried
  6. customgiving 32.4 g of crude product
  7. filtrationfiltered through celite
  8. additiondiluted with 300 ml of dichloromethane
  9. customto crystallize in a refrigerator
  10. filtrationThe solid is collected by filtration
  11. washwashed with acetone:dichloromethane (1:2) and air
  12. customdried
  13. customTwo more crops are recovered by essentially the same procedure
  14. temperatureThe combined solids are refluxed in 200 ml of acetone
  15. additionin a mixture of 700 ml of acetonitrile and 350 ml of methanol
  16. filtrationThe solid is recovered by filtration
  17. customdried at 110° C. overnight

Sources & evidence

ORD record
ord-057f8f094fae493482ace313f4068c78
Source dataset
uspto-grants-1983_01
Patent number
US04369191

Reaction notes

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