2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86691482, compound

HRID 576489Notes

Reaction equation

HRID 576489 reaction equation
[C:1]1([C:7]2[C:20]3[CH2:19][CH2:18][C:17]4[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=4[C:15]=3[N:14]=[C:13]3[C:8]=2[CH2:9][CH2:10][C:11]2[CH:28]=[CH:27][CH:26]=[CH:25][C:12]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>[C:1]1([C:7]2[C:20]3[CH:19]=[CH:18][C:17]4[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=4[C:15]=3[N:14]=[C:13]3[C:8]=2[CH:9]=[CH:10][C:11]2[CH:28]=[CH:27][CH:26]=[CH:25][C:12]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 349682257366-68-4

Product 1

HCID 86691482HCID 86691482, compound

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

2 (1.55 g, 4.31 mmol) was dissolved in 100 mL dioxane and 2,3-dichloro-5,6-dicyanobenzoquinone was added (6.88 g, 30.3 mmol). The mixture was refluxed under argon for 2 days. The reaction mixture was then cooled to room temperature, poured in 300 mL saturated aqueous sodium carbonate solution and stirred at 65° C. for 30 min. The mixture was then cooled to room temperature, the precipitation was filtered and washed with water and methylene chloride. Yield: 1.1 g (72%).

Workup

  1. temperatureThe mixture was refluxed under argon for 2 days
  2. temperatureThe mixture was then cooled to room temperature
  3. customthe precipitation
  4. filtrationwas filtered
  5. washwashed with water and methylene chloride

Sources & evidence

ORD record
ord-a403915429ec435a80205095f5d74c79
Source dataset
uspto-grants-2015_05
Patent number
US09040175B2

Reaction notes

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