HCID 12900263, compound → HCID 131712311, compound

HRID 894149Notes

Reaction equation

HRID 894149 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.[Cl:35][C:36]1[C:45]2[C:44]([S:46](Cl)(=[O:48])=[O:47])=[CH:43][C:42]([S:50](Cl)(=[O:52])=[O:51])=[CH:41][C:40]=2[C:39]([S:54](Cl)(=[O:56])=[O:55])=[CH:38][CH:37]=1>N1C=CC=CC=1>[Cl:35][C:36]1[CH:37]=[CH:38][C:39]([S:54]([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:56])=[O:55])=[C:40]2[C:45]=1[C:44]([S:46]([NH:1][C:2]1[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]=1)(=[O:48])=[O:47])=[CH:43][C:42]([S:50]([NH:1][C:2]1[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]=1)(=[O:52])=[O:51])=[CH:41]2

Participants

4

Reactant 2

HCID 12900263HCID 12900263, compoundHCID 12944552HCID 12944552, compound

Product 1

HCID 131712311HCID 131712311, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 13.6 g. of 5-amino-1,2,3-benzenetricarboxylic acid, triphenyl ester (U.S. Pat. No. 4,087,613) in 45 ml. of dry pyridine is added 4.58 g. of 8-chloro-1,3,5-naphthalenetrisulfonyl chloride, and the mixture is heated at 60°-70° C. for three hours. The cooled solution is added slowly with vigorous stirring to 300 ml. of ice-water, and the resulting solid is collected by filtration, washed with water, and dried. The solid is dissolved in methylene chloride, washed with water, and dried. The extract is concentrated to a volume of 80 ml. and passed through a bed of hydrous magnesium silicate. Evaporation of the filtrate with the addition of ether gives a solid, which is purified by chromatography on silica gel giving 7.8 g. of a light yellow solid.

Workup

  1. additionThe cooled solution is added slowly
  2. filtrationof ice-water, and the resulting solid is collected by filtration
  3. washwashed with water
  4. customdried
  5. dissolutionThe solid is dissolved in methylene chloride
  6. washwashed with water
  7. customdried
  8. concentrationThe extract is concentrated to a volume of 80 ml
  9. customEvaporation of the filtrate
  10. additionwith the addition of ether
  11. customgives a solid, which
  12. customis purified by chromatography on silica gel giving 7.8 g

Sources & evidence

ORD record
ord-afe37ee79f524225acc08ede44a3d2b8
Source dataset
uspto-grants-1981_08
Patent number
US04282375

Reaction notes

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