Toluene → Spiro[imidazolidine-4,1′(2′H)-naphthalene]-2,5-dione

HRID 482691Notes

Reaction equation

HRID 482691 reaction equation
C1(C)C=CC=CC=1.O[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]2([C:22](=[O:23])[NH:21][C:20](=[O:24])[NH:19]2)[CH2:11][CH2:10]1.C1(C)C(S(O)(=O)=O)=CC=CC=1>C(OCC)(=O)C>[C:12]12([C:22](=[O:23])[NH:21][C:20](=[O:24])[NH:19]1)[C:13]1[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:9]=[CH:10][CH2:11]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 69252-Methylbenzenesulfonic acidHCID 13563094HCID 13563094, compound

Product 1

HCID 20244915Spiro[imidazolidine-4,1′(2′H)-naphthalene]-2,5-dioneYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a refluxing solution of 100 ml. of toluene containing 4.5 g. (0.019 mole) of 3',4'-dihydro-4'-hydroxyspiro [imidazolidine-4,1'(2'H)-naphthalene]2,-5-dione was added a trace of -toluenesulfonic acid and the refluxing continued for 2 hours. The reaction was cooled, stripped to dryness and the residue dissolved in 100 ml. of ethyl acetate. The organic phase was washed with a saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated to dryness. The residue was triturated with diethyl ether, 2.7 g. (65% yield).

Workup

  1. temperatureThe reaction was cooled
  2. dissolutionthe residue dissolved in 100 ml
  3. washThe organic phase was washed with a saturated sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was triturated with diethyl ether, 2.7 g

Sources & evidence

ORD record
ord-043c0bb9cc8947c4a9bf94054d556f53
Source dataset
uspto-grants-1986_03
Patent number
US04575507

Reaction notes

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