Toluene → HCID 21432645, compound

HRID 2399095Notes

Reaction equation

HRID 2399095 reaction equation
[CH:1]12[C:11]3([Cl:15])[C:12]([Cl:14])([Cl:13])[C:8]([Cl:18])([C:9]([Cl:17])=[C:10]3[Cl:16])[CH:2]1[C:3]([O:5][C:6]2=[O:7])=O.C1(C)C=CC=CC=1.[SH:26][C:27]1[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=1[NH2:29]>O>[SH:26][C:27]1[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=1[N:29]1[C:6](=[O:7])[CH:1]2[CH:2]([C:8]3([Cl:18])[C:12]([Cl:13])([Cl:14])[C:11]2([Cl:15])[C:10]([Cl:16])=[C:9]3[Cl:17])[C:3]1=[O:5]

Participants

5

Reactant 3

HCID 1140TolueneHCID 8265Chlorendic anhydrideHCID 87132-Aminothiophenol

Product 1

HCID 21432645HCID 21432645, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 3000 ml 3-neck round bottom flask, equipped with a Dean-Stark water trap and a mechanical stirrer, was charged with 203.5 g (10% molar excess) of chlorendic anhydride and 1600 ml of toluene. Sixty-two grams of 2-mercaptoaniline was added to the resultant solution, whereupon a pale yellow suspension was formed. The reaction mixture was heated gradually until the solvent began to reflux and the evolution of water commenced and it was collected in the Dean-Stark water trap. The heating and refluxing were continued until the calculated amount of water, 9 ml. was collected, this requiring a total of 6 hours. At this point, there was no solid left in the reaction mixture. Solvent was then distilled to reduce the volume to about one-half. The residue, a clear solution, was then poured into 1000 ml of Skellysolve B (a mixture of hexanes, b. pt. = 146°-156° F., from Skelly Oil Co.) and the resultant solid was separated by filtration on a Buchner funnel and dried in air overnight. One crystallization from toluene gave white crystals of the dicarboximide with a melting point of 195°-8° C.

Workup

  1. customwas formed
  2. temperatureThe reaction mixture was heated gradually until the solvent
  3. temperatureto reflux
  4. customit was collected in the Dean-Stark water trap
  5. temperatureThe heating and refluxing
  6. customwas collected
  7. customa total of 6 hours
  8. waitleft in the reaction mixture
  9. distillationSolvent was then distilled
  10. additionThe residue, a clear solution, was then poured into 1000 ml of Skellysolve B (
  11. additiona mixture of hexanes, b. pt. = 146°-156° F.
  12. custom) and the resultant solid was separated by filtration on a Buchner funnel
  13. customdried in air overnight
  14. customOne crystallization from toluene

Sources & evidence

ORD record
ord-5cfe4f2c30bc4acea10beff180c79f9f
Source dataset
uspto-grants-1977_05
Patent number
US04026963

Reaction notes

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