O-Phenylenediamine → HCID 22495825, compound

HRID 2053374Notes

Reaction equation

HRID 2053374 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[C:6]([CH:10]=1)[C:7](Cl)=O.[C:22]1([NH2:29])[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH2:28]>C1(C)C=CC=CC=1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([NH:11][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:10][C:6]=2[C:7]2[NH:29][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:28]=2)(=[O:14])=[O:13])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 9842024HCID 9842024, compound

Product 1

HCID 22495825HCID 22495825, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.00 g (2.7 mmol) of 5-chloro-2-(4-chloro-phenylsulfonylamino)-benzoyl chloride and 296 mg (2.7 mmol) of o-phenylenediamine in 150 ml of toluene were heated under reflux for 1 h. A small amount of solid was filtered off with suction and the filtrate was evaporated. The residue was taken up in 50 ml of toluene, 600 mg of thionyl chloride were added and the mixture was again heated under reflux for 10 h. Subsequently it was cooled and the precipitated solid was filtered off with suction. 280 mg (25%) of the title compound having a melting point of 225-228° C. were obtained.

Workup

  1. temperatureunder reflux for 1 h
  2. filtrationA small amount of solid was filtered off with suction
  3. customthe filtrate was evaporated
  4. addition600 mg of thionyl chloride were added
  5. temperaturethe mixture was again heated
  6. temperatureunder reflux for 10 h
  7. temperatureSubsequently it was cooled
  8. filtrationthe precipitated solid was filtered off with suction
  9. customwere obtained

Sources & evidence

ORD record
ord-8568121c6d334f47b74e586b45787e89
Source dataset
uspto-grants-2008_02
Patent number
US07326789B2

Reaction notes

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