Tetrachlorophthalic anhydride → HCID 12852398, compound

HRID 1702596Notes

Reaction equation

HRID 1702596 reaction equation
[Cl:1][C:2]1[C:3]([Cl:15])=[C:4]([Cl:14])[C:5]([Cl:13])=[C:6]2[C:11](=[O:12])[O:10][C:8](=[O:9])[C:7]=12.[F:16][C:17]([F:29])([F:28])[S:18]([C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>>[F:28][C:17]([F:16])([F:29])[S:18]([C:21]1[CH:22]=[CH:23][C:24]([NH:25][C:11](=[O:12])[C:6]2[C:7](=[C:2]([Cl:1])[C:3]([Cl:15])=[C:4]([Cl:14])[C:5]=2[Cl:13])[C:8]([OH:10])=[O:9])=[CH:26][CH:27]=1)(=[O:19])=[O:20]

Participants

3

Reactant 2

HCID 8326Tetrachlorophthalic anhydrideHCID 1363154-Aminophenyl trifluoromethyl sulphone

Product 1

HCID 12852398HCID 12852398, compoundYield 56%

Procedure

14 g (0.05 mol) of tetrachlorophthalic anhydride and 11 g (0.05 mol) of 4-trifluoromethylsulphonylaniline were heated to 200° C. and the mixture was kept at this temperature for 2 hours. It was then cooled and the reaction product was precipitated by adding ice-water. The product was then filtered off, washed with 50 ml of methanol and then stirred with 10% strength sodium hydroxide solution until it had dissolved. The impurities were filtered off and aqueous dilute hydrochloric acid was added to the filtrate. The crystals thereby obtained were filtered off and dried at 50° C. 14 g (that is to say 56% of theory) of N-(4-trifluoromethylsulphonylphenyl)-tetrachlorophthalamic acid of melting point 92°-97° C. were obtained.

Workup

  1. temperatureIt was then cooled
  2. customthe reaction product was precipitated
  3. additionby adding ice-water
  4. filtrationThe product was then filtered off
  5. washwashed with 50 ml of methanol
  6. dissolutionhad dissolved
  7. filtrationThe impurities were filtered off
  8. additionaqueous dilute hydrochloric acid was added to the filtrate
  9. customThe crystals thereby obtained
  10. filtrationwere filtered off
  11. customdried at 50° C

Sources & evidence

ORD record
ord-c691bc781c164ee7beee5b9670d7c649
Source dataset
uspto-grants-1982_09
Patent number
US04348411

Reaction notes

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