2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 17839501, compound

HRID 600133Notes

Reaction equation

HRID 600133 reaction equation
[CH2:1]([C:4]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]([CH2:20][CH2:21][CH3:22])=[C:12]2[C:17]=1[CH:16]=[C:15]([I:18])[C:14]([I:19])=[CH:13]2)[CH2:2][CH3:3].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH2:20]([C:11]1[C:10]2[C:5]([C:4]([CH2:1][CH2:2][CH3:3])=[C:17]3[C:12]=1[CH:13]=[C:14]([I:19])[C:15]([I:18])=[CH:16]3)=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 15530753HCID 15530753, compound

Product 1

HCID 17839501HCID 17839501, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

9,10-Dipropyl-2,3-diiodo-5,6,7,8-tetrahydroanthracene (0.259 g, 0.5 mmol), 2,3-dichloro-5,6-dicyanobenzoquinone (0.341 g, 1.5 mmol) and 1,4-dioxane (3 ml) were charged in a reactor. Then, the mixture was refluxed for an hour. After cooling, the precipitates were removed by filtration. The solvent in the mixture was removed in vacuum. Column chromatography (hexane) was performed to give the title compound (0.109 g) as a light yellow solid. The isolation yield was 42%.

Workup

  1. temperatureThen, the mixture was refluxed for an hour
  2. temperatureAfter cooling
  3. customthe precipitates were removed by filtration
  4. customThe solvent in the mixture was removed in vacuum

Sources & evidence

ORD record
ord-16e7a4d4ddbd497fb0ae0f42853ae0c8
Source dataset
uspto-grants-2011_03
Patent number
US07901594B2

Reaction notes

Loading…