2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 69754075, compound

HRID 1816458Notes

Reaction equation

HRID 1816458 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:36])[NH:17][C:18]([N:21]3[C:29]4[C:28]5[CH:30]=[C:31]([O:34][CH3:35])[CH:32]=[CH:33][C:27]=5[CH2:26][CH2:25][C:24]=4[CH:23]=[N:22]3)([CH3:20])[CH3:19])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.C([O-])(O)=O.[Na+]>O1CCOCC1>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16](=[O:36])[NH:17][C:18]([N:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]5[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:28]5=4)[CH:23]=[N:22]3)([CH3:20])[CH3:19])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 516892Sodium BicarbonateHCID 69752194HCID 69752194, compound

Product 1

HCID 69754075HCID 69754075, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of the product from Step A (0.08 g, 0.17 mmol) in 1,4-dioxane (10 mL) was added DDQ (0.08 g, 0.34 mmol). The solution was stirred at 23° C. for 3 hr and poured into saturated aqueous NaHCO3 and this mixture was extracted with ether (2×20 mL). The combined extracts were washed with aqueous NaHCO3, dried (MgSO4), and evaporated to a crude product which was purified by chromatography (silica, 40% ethyl acetate in hexanes) to obtain an oil (0.045 g, 55%): MS m/z: 478 [M+H]+.

Workup

  1. extractionthis mixture was extracted with ether (2×20 mL)
  2. washThe combined extracts were washed with aqueous NaHCO3
  3. dry with materialdried (MgSO4)
  4. customevaporated to a crude product which
  5. customwas purified by chromatography (silica, 40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5450311a5543427f9bfc674b1c65e40c
Source dataset
uspto-grants-2005_04
Patent number
US06884816B2

Reaction notes

Loading…