Toluene → HCID 21432646, compound

HRID 2399096Notes

Reaction equation

HRID 2399096 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][C:30]([NH2:31])=[CH:29][CH:28]=1>O.O1CCOCC1>[SH:26][C:27]1[CH:33]=[CH:32][C:30]([N:31]2[C:6](=[O:7])[CH:1]3[CH:2]([C:8]4([Cl:18])[C:12]([Cl:13])([Cl:14])[C:11]3([Cl:15])[C:10]([Cl:16])=[C:9]4[Cl:17])[C:3]2=[O:5])=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 8265Chlorendic anhydrideHCID 145104-Aminothiophenol

Product 1

HCID 21432646HCID 21432646, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A 1000 ml 3-neck flask, equipped with a Dean-Stark water trap and a mechanical stirrer, was charged with 102 g (10% molar excess) of chlorendic anhydride, 400 ml toluene and 300 ml of dry dioxane. Thirty-one grams of 4-mercaptoaniline were then added to the resultant solution, whereupon a pale yellow solid formed instantly. The reaction mixture was heated gradually until the solvent began to reflux, at which point the evolution of water commenced and the solid disappeared. About 4.5 ml of water were collected in about 3 hours. Solvent was then distilled to reduce the volume to about one-half its original volume. The resultant solution, when cooled to room temperature, deposited white crystals of the carboximide. The crystals were separated by filtration and dried overnight at room temperature. The melting point of the carboximide was 237°-240° C.

Workup

  1. customformed instantly
  2. temperatureThe reaction mixture was heated gradually until the solvent
  3. temperatureto reflux, at which
  4. customAbout 4.5 ml of water were collected in about 3 hours
  5. distillationSolvent was then distilled
  6. customThe crystals were separated by filtration
  7. customdried overnight at room temperature
  8. customwas 237°-240° C.

Sources & evidence

ORD record
ord-9f5d262d66d248e58958d941c7e6750e
Source dataset
uspto-grants-1977_05
Patent number
US04026963

Reaction notes

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