2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 18406506, compound

HRID 1016320Notes

Reaction equation

HRID 1016320 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6]4=[C:7]([C:18](=[O:28])[C:19](CC5C=NC=CC=5)=[CH:20][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:16][CH3:17])[CH:10]=3.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[OH-].[Na+].C(OCC)(=O)C>O1CCOCC1>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6]4=[C:7]([C:18](=[O:28])[CH:19]=[CH:20][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:16][CH3:17])[CH:10]=3

Participants

6

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 12021104HCID 12021104, compound

Product 1

HCID 18406506HCID 18406506, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The compound (2 g) obtained in Example 36 <step 2> was suspended in dioxane (110 mL) and to the suspension was added DDQ (1.88 g). The mixture was heated under reflux for 3 hours. After allowing to cool, to the mixture were added 1N-sodium hydroxide (20 mL) and ethyl acetate(50 mL) . The precipitate crystals were collected by filtration and washed with water and ethanol in turns to obtain the title compound (1.41 g; 71%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool, to the mixture
  4. filtrationThe precipitate crystals were collected by filtration
  5. washwashed with water and ethanol in turns

Sources & evidence

ORD record
ord-f7642e6bcae4404daceda3abdf0dc5f9
Source dataset
uspto-grants-2002_11
Patent number
US06476021B1

Reaction notes

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