1,6-Cleve's acid → HCID 12094653, compound

HRID 480669

Reaction equation

HRID 480669 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:7]2.[N+:16]([C:19]1[CH:20]=[C:21]([C:28](Cl)=[O:29])[CH:22]=[C:23]([C:25](Cl)=[O:26])[CH:24]=1)([O-:18])=[O:17]>N1C=CC=CC=1.O1CCOCC1.C(Cl)(Cl)Cl>[N+:16]([C:19]1[CH:20]=[C:21]([C:28]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6]([S:12]([OH:15])(=[O:13])=[O:14])=[CH:7]3)=[O:29])[CH:22]=[C:23]([C:25](=[O:26])[NH:1][C:2]2[C:3]3[C:8](=[CH:7][C:6]([S:12]([OH:15])(=[O:13])=[O:14])=[CH:5][CH:4]=3)[CH:9]=[CH:10][CH:11]=2)[CH:24]=1)([O-:18])=[O:17]

Participants

6

Reactant 2

HCID 84081,6-Cleve's acidHCID 834515-Nitroisophthaloyl chloride

Product 1

HCID 12094653HCID 12094653, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

22.33 g (0.10 mol) of 5-amino-2-naphthalenesulfonic acid was suspended in 150 mL of pyridine and added to the above di-acid chloride in 50 mL (50:50) of dioxane and CHCl3 under vigorous stirring for 1-2 hrs. The crude product was precipitated with dioxane. The oily product was collected on a Büchner funnel. The brown colored oily product was dissolved in 500 mL water, then allowed to precipitate out over 30 min. The solid material was collected using filtration. It yielded 16.2 g.

Workup

  1. customThe crude product was precipitated with dioxane
  2. customThe oily product was collected on a Büchner funnel
  3. dissolutionThe brown colored oily product was dissolved in 500 mL water
  4. customto precipitate out over 30 min
  5. customThe solid material was collected
  6. filtrationfiltration
  7. customIt yielded 16.2 g

Sources & evidence

ORD record
ord-5e3368348bc7428f8858fabd35c3d318
Source dataset
uspto-grants-2003_11
Patent number
US06653321B1

Linked notes

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