4-Sulfophthalic acid → Phthaloperinone sulphochloride

HRID 2398070

Reaction equation

HRID 2398070 reaction equation
[S:1]([C:5]1[C:6](=[O:25])[C:7]2[N:8]3[C:16]([N:17]=[C:18]4[C:24]=2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19]4)=[C:15]1[C:10]([CH:11]=[CH:12][CH:13]=[CH:14]1)=[CH:9]3)([OH:4])(=[O:3])=[O:2].S(C1C=C(C(O)=O)C(=CC=1)C(O)=O)(O)(=O)=O.C1C=C(N)C2C(N)=CC=CC=2C=1.P(Cl)(Cl)([Cl:56])=O>CN1CCCC1=O.C1(C)C(C)=CC=CC=1>[C:6]1(=[O:25])[C:7]2=[C:24]3[C:18](=[N:17][C:16]4[N:8]2[CH:9]=[C:10]2[C:15]=4[CH:14]=[CH:13][CH:12]=[CH:11]2)[CH:19]=[CH:20][CH:21]=[C:22]3[CH:23]=[CH:5]1.[S:1]([Cl:56])([OH:4])(=[O:3])=[O:2]

Participants

7

Reactant 4

HCID 69624-Sulfophthalic acidHCID 24813Phosphorus oxychlorideHCID 680671,8-DiaminonaphthaleneHCID 21434658Sulphophthaloperinone

Product 1

HCID 86734752Phthaloperinone sulphochlorideYield 91.4%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

11.5 g of sulphophthaloperinone, prepared from 4-sulphophthalic acid and 1,8-naphthylenediamine in N-methylpyrrolidone, are suspended in 100 ml of xylene. 9.2 g of phosphorus oxychloride are added and the mixture is heated to 80° C for 6 - 7 hours, whilst stirring. 25 - 30 ml of xylene are then distilled off under reduced pressure and after cooling the reaction product which has precipitated is filtered off and the residue is rinsed with petroleum ether. 11.6 g of phthaloperinone-sulphochloride are obtained.

Workup

  1. distillation25 - 30 ml of xylene are then distilled off under reduced pressure
  2. temperatureafter cooling the reaction product which
  3. customhas precipitated
  4. filtrationis filtered off
  5. washthe residue is rinsed with petroleum ether

Sources & evidence

ORD record
ord-81a6fe1d67a5465a8a61445368ca5662
Source dataset
uspto-grants-1977_05
Patent number
US04024144

Linked notes

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