p-Toluenesulfonic acid → 2-[(3-Iminoisoindol-1-yl)methylene]-3-methyl thiazolinium p-toluene sulfonate

HRID 462510Notes

Reaction equation

HRID 462510 reaction equation
N=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[NH:11])[NH:3]1.[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:17][CH:18]=1>CO>[C:13]1([CH3:12])[CH:14]=[CH:15][C:16]([S:19]([O-:22])(=[O:20])=[O:21])=[CH:17][CH:18]=1.[NH:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([CH:10]=[C:2]2[N+:3]([CH3:4])=[CH:17][CH2:16][S:19]2)=[N:3]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 178508669HCID 178508669, compound

Product 1

HCID 886668552-[(3-Iminoisoindol-1-yl)methylene]-3-methyl thiazolinium p-toluene sulfonate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Three grams of 1,3-diiminoisoindoline were dissolved in 25 ml of methanol. The solution was treated with 5.7 grams of 2,3-dimethyl thiazolinine p-toluenesulfonate which had been dissolved in 25 ml of methanol. The resulting mixture was heated at reflux for several hours. A yellow solid was obtained upon cooling and scratching the vessel. The solid was collected and washed free of the dark colored mother liquor with methanol and acetone. The dye was then dissolved in hot water from which it was recrystallized. The dye can be converted to other salts by adding an anion, such as iodide, to give a more insoluble salt.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for several hours
  3. customA yellow solid was obtained
  4. temperatureupon cooling
  5. customThe solid was collected
  6. washwashed free of the dark colored mother liquor with methanol and acetone
  7. dissolutionThe dye was then dissolved in hot water from which it
  8. customwas recrystallized
  9. additionby adding an anion

Sources & evidence

ORD record
ord-944937890ef04169bf897531ece2eb8a
Source dataset
uspto-grants-1985_05
Patent number
US04515955

Reaction notes

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