Dimethylformamide → HCID 70654232, compound

HRID 2205157Notes

Reaction equation

HRID 2205157 reaction equation
C[N:2](C=O)C.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:23]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)=[N:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([S:32]([OH:35])(=O)=[O:33])[CH:20]=3)[N:15]=2)=[CH:10][CH:9]=1>S(Cl)(Cl)=O>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:23]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)=[N:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([S:32]([NH2:2])(=[O:35])=[O:33])[CH:20]=3)[N:15]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 86670229HCID 86670229, compound

Product 1

HCID 70654232HCID 70654232, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

DMF (2 mL) was added dropwise with stirring to a solution of 2,3-bis(4-methoxyphenyl)quinoxaline-6-sulfonic acid (137.2 mg, 0.33 mmol, 1.00 equiv) in thionyl chloride (12 mL), stirred at reflux for 3 h in an oil bath, then concentrated under vacuum. The residue was dissolved in acetonitrile (10 mL), and added dropwise to a solution of ammonia (2 g) in acetonitrile (10 mL) at 0° C. The resulting mixture was stirred for overnight at room temperature. The reaction mixture was concentrated under vacuum and purified via Prep-HPLC affording 16 mg (12%) of 2,3-bis(4-methoxyphenyl)quinoxaline-6-sulfonamide as a light yellow solid.

Workup

  1. temperatureat reflux for 3 h in an oil bath
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in acetonitrile (10 mL)
  4. additionadded dropwise to a solution of ammonia (2 g) in acetonitrile (10 mL) at 0° C
  5. stirringThe resulting mixture was stirred for overnight at room temperature
  6. concentrationThe reaction mixture was concentrated under vacuum
  7. custompurified via Prep-HPLC

Sources & evidence

ORD record
ord-594bf224e2b949ddb2c4fda66bf4099d
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

Loading…