2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 10205325, compound

HRID 900738Notes

Reaction equation

HRID 900738 reaction equation
C(C1C(=O)C(Cl)=C(Cl)C(=[O:6])C=1C#N)#N.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH2:24][C:25]2[S:40][C:28]3[N:29]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:30](=[O:35])[N:31]([CH3:34])[C:32](=[O:33])[C:27]=3[C:26]=2[C:41]([N:43]([O:45][CH3:46])[CH3:44])=[O:42])=[CH:16]1>C1COCC1.O>[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([C:24]([C:25]2[S:40][C:28]3[N:29]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:30](=[O:35])[N:31]([CH3:34])[C:32](=[O:33])[C:27]=3[C:26]=2[C:41]([N:43]([O:45][CH3:46])[CH3:44])=[O:42])=[O:6])=[CH:16]1

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 10161330HCID 10161330, compound

Product 1

HCID 10205325HCID 10205325, compoundYield 38.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

DDQ (0.25 g) was added to a stirred solution of the product of example 4 (0.25 g) in THF (9 ml) and water (1 ml). The solution was stirred for a further 2 h and the concentrated in vacuo. The residue was purified by flash silica chromatography eluting with ethyl acetate:isohexane (7:3) to give the title compound as a pale pink solid (0.1 g).

Workup

  1. concentrationthe concentrated in vacuo
  2. customThe residue was purified by flash silica chromatography
  3. washeluting with ethyl acetate:isohexane (7:3)

Sources & evidence

ORD record
ord-1db6b31c964541ccb6d1fd6c81c29aad
Source dataset
uspto-grants-2008_04
Patent number
US07361660B2

Reaction notes

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