2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 178518065, compound

HRID 1526494Notes

Reaction equation

HRID 1526494 reaction equation
[C:1]12[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=1[S:8][C:7]1[N:6]=[CH:5][N:4]=[C:3]([OH:14])[C:2]2=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[C:1]12[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:8][C:7]1[N:6]=[CH:5][N:4]=[C:3]([OH:14])[C:2]2=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 178518064HCID 178518064, compound

Product 1

HCID 178518065HCID 178518065, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-3-ol (2.06 g, 9.99 mmol, 1.00 equiv) in 1,4-dioxane (30 mL) was added DDQ (5.68 g, 25.02 mmol, 2.50 equiv) ar room temperature under nitrogen and the resulting solution was stirred overnight at 90° C. in an oil bath. After cooling to room temperature, the reaction was quenched with saturated aqueous sodium bicarbonate, and extracted with 3×100 mL of dichloromethane. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum to provide 1.8 g (crude) of 8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5,10,12-hexaen-3-ol as a yellow solid.

Workup

  1. customar room temperature under nitrogen
  2. temperatureAfter cooling to room temperature
  3. customthe reaction was quenched with saturated aqueous sodium bicarbonate
  4. extractionextracted with 3×100 mL of dichloromethane
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0f4444ec6c224f5a9bba4c996d62a014
Source dataset
uspto-grants-2015_07
Patent number
US09085586B2

Reaction notes

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