Water → HCID 68905772, compound

HRID 2099892Notes

Reaction equation

HRID 2099892 reaction equation
O.[Si:2]([O:19][CH2:20][C@:21]12[C@H:27]([O:28]CC3C4C(=CC=CC=4)C=CC=3)[C@H:24]([O:25][CH2:26]1)[C@H:23]([N:40]1[CH:47]=[CH:46][C:44](=[O:45])[NH:43][C:41]1=[O:42])[O:22]2)([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl>[Si:2]([O:19][CH2:20][C@:21]12[C@H:27]([OH:28])[C@H:24]([O:25][CH2:26]1)[C@H:23]([N:40]1[CH:47]=[CH:46][C:44](=[O:45])[NH:43][C:41]1=[O:42])[O:22]2)([C:15]([CH3:17])([CH3:16])[CH3:18])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 131727561HCID 131727561, compound

Product 1

HCID 68905772HCID 68905772, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Water (23 mL) was added to Compound 109 (11.8 g) dissolved in CH2Cl2 (120 mL) and the biphasic solution was stirred at room temperature. To this stirring solution was added DDQ (9.2 g) and the reaction mixture was stirred for 7 h at which point the reaction was complete. The reaction mixture was diluted with dichloromethane (500 mL) and it washed with 2% aqueous sodium bisulfite solution. The organic layer was separated and the aqueous layer was extracted several times with dichloromethane. The combined organic layer was washed with saturated sodium bicarbonate solution (5×300 mL). The organic layer was dried over anhydrous sodium sulfate and the solvent removed under reduced pressure. The residue was purified by using 30% EtOAc in CH2Cl2 followed by 10% MeOH in CH2Cl2. Compound 110 obtained in a 96% yield as colorless pallets after removing the solvent.

Workup

  1. stirringthe reaction mixture was stirred for 7 h at which
  2. washwashed with 2% aqueous sodium bisulfite solution
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted several times with dichloromethane
  5. washThe combined organic layer was washed with saturated sodium bicarbonate solution (5×300 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent removed under reduced pressure
  8. customThe residue was purified

Sources & evidence

ORD record
ord-6c8108436ec646058a7c1067bf9827b4
Source dataset
uspto-grants-2009_08
Patent number
US07569686B1

Reaction notes

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