2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 17839517, compound

HRID 600138Notes

Reaction equation

HRID 600138 reaction equation
[CH2:1]([C:4]1[C:21]2[CH2:20][C:19]3[C:14](=[C:15]([CH2:31][CH2:32][CH3:33])[C:16]([CH2:28][CH2:29][CH3:30])=[C:17]([CH2:25][CH2:26][CH3:27])[C:18]=3[CH2:22][CH2:23][CH3:24])[CH2:13][C:12]=2[C:11]([CH2:34][CH2:35][CH3:36])=[C:10]2[C:5]=1[CH:6]=[C:7]([I:38])[C:8]([I:37])=[CH:9]2)[CH2:2][CH3:3].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[I:37][C:8]1[C:7]([I:38])=[CH:6][C:5]2[C:10](=[C:11]([CH2:34][CH2:35][CH3:36])[C:12]3[C:21]([C:4]=2[CH2:1][CH2:2][CH3:3])=[CH:20][C:19]2[C:14](=[C:15]([CH2:31][CH2:32][CH3:33])[C:16]([CH2:28][CH2:29][CH3:30])=[C:17]([CH2:25][CH2:26][CH3:27])[C:18]=2[CH2:22][CH2:23][CH3:24])[CH:13]=3)[CH:9]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 17839508HCID 17839508, compound

Product 1

HCID 17839517HCID 17839517, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6,11-Dihydro-5,7,8,9,10,12-hexapropyl-2,3-diiodonaphthacene (0.23 8 g, 0.324 mmol), 2,3-dichloro-5,6-dicyanobenzoquinone (0.081 g, 0.35 mmol) and 1,4-dioxane (2 ml) were charged in a reactor. The mixture was refluxed for 3 hours. After cooling, the precipitates were removed by filtration. The solvent in the mixture was removed in vacuum followed by recrystallization from chloroform/methanol. The orange red title compound (0.081 g) was obtained. The isolation yield was 34%.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. temperatureAfter cooling
  3. customthe precipitates were removed by filtration
  4. customThe solvent in the mixture was removed in vacuum
  5. customfollowed by recrystallization from chloroform/methanol

Sources & evidence

ORD record
ord-0a2ae88757314acd8f2e467460477222
Source dataset
uspto-grants-2011_03
Patent number
US07901594B2

Reaction notes

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