Water → 2-(3-Pentafluorosulfanylphenyl)isoindole-1,3-dione

HRID 2356659Notes

Reaction equation

HRID 2356659 reaction equation
[F:1][S:2]([F:13])([F:12])([F:11])([F:10])[C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1.[C:14]1(=O)[O:19][C:17](=[O:18])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.O>C(O)(=O)C>[F:1][S:2]([F:10])([F:11])([F:12])([F:13])[C:3]1[CH:4]=[C:5]([N:9]2[C:17](=[O:18])[C:16]3[C:15](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:14]2=[O:19])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 27791883-(Pentafluoro-lambda6-sulfanyl)aniline

Product 1

HCID 596421532-(3-Pentafluorosulfanylphenyl)isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.5 g (6.84 mmol) of 3-pentafluorosulfanylphenylamine 51.3 were suspended with 1.01 g (6.84 mmol) of phthalic anhydride in 4 ml of acetic acid and boiled under reflux for 2 h. The cooled reaction mixture was admixed with 40 ml of water, treated in an ultrasound bath for 30 min and filtered. The residue was washed with water and then with a little ethanol, and dried under reduced pressure. 2-(3-Pentafluorosulfanylphenyl)isoindole-1,3-dione 51.4 with the melting point of 188-190° C. was obtained.

Workup

  1. temperatureunder reflux for 2 h
  2. customThe cooled reaction mixture
  3. additiontreated in an ultrasound bath for 30 min
  4. filtrationfiltered
  5. washThe residue was washed with water
  6. dry with materialwith a little ethanol, and dried under reduced pressure

Sources & evidence

ORD record
ord-77d93ab41a88428f807e2b71c4694ab8
Source dataset
uspto-grants-2010_07
Patent number
US07759366B2

Reaction notes

Loading…