Chloranil → HCID 3335773, compound

HRID 1380282Notes

Reaction equation

HRID 1380282 reaction equation
[C:1]1(Cl)[C:7](=[O:8])[C:6](Cl)=[C:5](Cl)[C:3](=[O:4])[C:2]=1Cl.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.[K]>C(#N)C.CN(C)C=O>[C:13]1(=[O:23])[N:17]([C:1]2[C:7](=[O:8])[C:6]([N:17]3[C:13](=[O:23])[C:14]4=[CH:22][CH:21]=[CH:20][CH:19]=[C:15]4[C:16]3=[O:18])=[C:5]([N:17]3[C:13](=[O:23])[C:14]4=[CH:22][CH:21]=[CH:20][CH:19]=[C:15]4[C:16]3=[O:18])[C:3](=[O:4])[C:2]=2[N:17]2[C:16](=[O:18])[C:15]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]3[C:13]2=[O:23])[C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12

Participants

5

Reactant 2

HCID 8371ChloranilHCID 24194345Phthalimide potassium salt

Product 1

HCID 3335773HCID 3335773, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of chloranil (10.00 g, 0.04 mole) and potassium phthalimide (30.00 g, 0.16 mole) in acetonitrile is refluxed overnight. The deep purple solution is allowed to cool and then filtered, yielding a tan solid. This solid is then boiled in approximately 200 ml of dimethylformamide for ten minutes. The hot DMF suspension is then filtered yielding a white thixotropic solid.

Workup

  1. temperatureis refluxed overnight
  2. temperatureto cool
  3. filtrationfiltered
  4. customyielding a tan solid
  5. filtrationThe hot DMF suspension is then filtered
  6. customyielding a white thixotropic solid

Sources & evidence

ORD record
ord-4f104052e77947099da9ed2864aa4cf1
Source dataset
uspto-grants-1986_04
Patent number
US04581349

Reaction notes

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