4,4'-Dimethoxybenzil → HCID 86670229, compound

HRID 1405335Notes

Reaction equation

HRID 1405335 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=O)=[CH:5][CH:4]=1.[NH2:21][C:22]1[CH:23]=[C:24]([S:29]([OH:32])(=[O:31])=[O:30])[CH:25]=[CH:26][C:27]=1[NH2:28]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[N:21][C:22]3[C:27](=[CH:26][CH:25]=[C:24]([S:29]([OH:32])(=[O:30])=[O:31])[CH:23]=3)[N:28]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 710434,4'-DimethoxybenzilHCID 81986Benzenesulfonic acid, 3,4-diamino-

Product 1

HCID 86670229HCID 86670229, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1,2-bis(4-methoxyphenyl)ethane-1,2-dione (200 mg, 0.74 mmol) in ethanol (3 mL) and water (3 mL) was added 3,4-diaminobenzene-1-sulfonic acid (116 mg, 0.62 mmol). The resulting solution was stirred overnight at 100° C. in an oil bath, and then quenched by the addition of water (60 mL), extracted with dichloromethane (3×20 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo to afford 2,3-bis(4-methoxyphenyl)quinoxaline-6-sulfonic acid (95.3 mg, 30.4%).

Workup

  1. customquenched by the addition of water (60 mL)
  2. extractionextracted with dichloromethane (3×20 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-205f1eb912f84c6f9d465a67df6c9fae
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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