Phthalic Anhydride → HCID 131718923, compound

HRID 1608914Notes

Reaction equation

HRID 1608914 reaction equation
[NH2:1][C:2]1C=[C:4]2[C:9](=[CH:10][CH:11]=1)C(S(O)(=O)=O)=CC=C2.[C:16]1(=[O:26])[O:21][C:19](=O)[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[Na+].[NH2:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[C:35]([S:39]([O-:42])(=[O:41])=[O:40])=[CH:34][CH:33]=[CH:32]2.C([NH+](CC)CC)C>N1C=CC=CC=1>[NH+:1]1[CH:2]=[CH:11][CH:10]=[CH:9][CH:4]=1.[C:19]1(=[O:21])[N:28]([C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[C:35]([S:39]([O-:42])(=[O:40])=[O:41])=[CH:34][CH:33]=[CH:32]3)[C:16](=[O:26])[C:17]2=[CH:25][CH:24]=[CH:23][CH:22]=[C:18]12

Participants

6

Reactant 4

HCID 6811Phthalic AnhydrideHCID 664706-Aminonaphthalene-1-sulphonic acidHCID 1385867TriethylammoniumHCID 23696805Sodium 6-aminonaphthalene-1-sulphonate

Product 1

HCID 131718923HCID 131718923, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

223 g (1 mol) of 6-amino-1-naphthalenesulfonic acid and 148 g (1 mol) of phthalic anhydride are boiled for 0.5 h in 1 liter of pyridine. After boiling, the reaction mixture is left at room temperature for 16 h. The precipitated product is filtered and washed with pyridine and water, and then recrystallized from boiling water. Yield 298 g (69%); mp 234°-237° C.; Anal. Calcd. for C23H16N2SO5 :C 63.88, H 3.73, N 6.48, S 7.42; Found:C 63.74, H 3.81, N 6.52, S 6.99. When the 6-phthalimido-1-naphthalenesulfonic acid pyridinium salt was synthesized starting from 6-amino-1-naphthalenesulfonic acid sodium salt or triethylammonium salt, the calculated yields were 63% and 58% respectively.

Workup

  1. filtrationThe precipitated product is filtered
  2. washwashed with pyridine and water
  3. customrecrystallized
  4. customthe calculated yields

Sources & evidence

ORD record
ord-05251847db624057a3846b096fcc6b76
Source dataset
uspto-grants-1995_03
Patent number
US05399487

Reaction notes

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