2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 131727552, compound

HRID 2099881Notes

Reaction equation

HRID 2099881 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C1(C[O:26][C@@H:27]2[C@@:31]3([CH2:38][O:39][C@H:28]2[C@:29]([SiH:48]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)([N:40]2[CH:47]=[CH:46][C:44](=[O:45])[NH:43][C:41]2=[O:42])[O:30]3)[CH2:32][O:33][C:34]([CH3:37])([CH3:36])[CH3:35])C2C(=CC=CC=2)C=CC=1>C(Cl)Cl.O>[C:34]([O:33][CH2:32][C@@:31]12[CH2:38][O:39][C@@H:28]([C@:29]([SiH:48]([C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=3)[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)([N:40]3[CH:47]=[CH:46][C:44](=[O:45])[NH:43][C:41]3=[O:42])[O:30]1)[C@@H:27]2[OH:26])([CH3:37])([CH3:35])[CH3:36]

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 178450401HCID 178450401, compound

Product 1

HCID 131727552HCID 131727552, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (15.9 g, 70.0 mmol) was added to a mixture of compound 11 (19.7 g, 31.1 mmol) in CH2Cl2 (200 mL) and H2O (40 mL). After 7 hours of vigorous stirring at room temperature, the mixture was poured into CH2Cl2 (1 L). The resulting solution was washed with 2% (w/v) aqueous sodium bisulfite, followed by saturated aqueous NaHCO3, then dried over anhydrous Na2SO4, filtered, then evaporated to a light-brown foam. Purification by silica gel chromatography (2.5 vol. % methanol in CH2Cl2) yielded 15.0 g (97%) of 12 as an off-white foam.

Workup

  1. washThe resulting solution was washed with 2% (w/v) aqueous sodium bisulfite
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated to a light-brown foam
  5. customPurification by silica gel chromatography (2.5 vol. % methanol in CH2Cl2)

Sources & evidence

ORD record
ord-cd20ef58a0c84ce18210d6b3814bc65f
Source dataset
uspto-grants-2009_08
Patent number
US07569686B1

Reaction notes

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