2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 14962127, compound

HRID 515914Notes

Reaction equation

HRID 515914 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:15][C:16]([CH3:18])=[CH2:17])[CH2:12]C=C)(=[O:10])=[O:9])=[CH:4][CH:3]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[CH3:18][C:16]1[CH:17]=[CH:12][N:11]([S:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)(=[O:9])=[O:10])[CH:15]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 11230883Benzenesulfonamide, 4-methyl-N-(2-methyl-2-propenyl)-N-2-propenyl-

Product 1

HCID 14962127HCID 14962127, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of the compound obtained in Step B (15.2 g, 57.3 mmol) in toluene (550 mL) is heated at 80° C. in the presence of (1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)-dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium (Grubbs' catalyst, 2nd generation) (150 mg, 0.18 mmol) for 1 hour. 2,3-Dichloro-5,6-dicyano-p-benzoquinone (16.1 g, 70.9 mmol) is then added in one portion, and the solution is heated at 80° C. for 24 hours. The solution is filtered over Celite, and the filtrate is concentrated in vacuo. The product is purified by chromatography over silica gel using ethyl acetate and heptane as eluants to obtain the expected compound in the form of a solid.

Workup

  1. filtrationThe solution is filtered over Celite
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe product is purified by chromatography over silica gel

Sources & evidence

ORD record
ord-12a3a70934474e4484780477ca929e7b
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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