p-Fluoronitrobenzene → HCID 23146830, compound

HRID 1715536Notes

Reaction equation

HRID 1715536 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[NH2:25])[N:9]=2)=[CH:4][CH:3]=1.F[C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1.C(O[K])(C)(C)C>CS(C)=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]([C:18]3[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=3)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[NH:25][C:27]3[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 22638468HCID 22638468, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 23146830HCID 23146830, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

While agitating 3.0 g (9.2 mmol) of 2,3-di(4-methyl-phenyl)-5-aminoquinoxaline, 1.4 g (9.9 mmol) of 4-fluoronitrobenzene and 100 ml of dimethylsulfoxide, 3.4 g (30.3 mmol) of t-butoxy potassium was gently added. After completion of the addition, the reaction container was purged with nitrogen, followed by agitation at room temperature for 20 hours. After completion of the reaction, 100 ml of water was added while cooling, and an organic phase was extracted by use of a chloroform solvent, followed by concentration to obtain the intended product.

Workup

  1. additionwas gently added
  2. additionAfter completion of the addition
  3. customthe reaction container was purged with nitrogen
  4. customAfter completion of the reaction, 100 ml of water
  5. additionwas added
  6. temperaturewhile cooling
  7. extractionan organic phase was extracted by use of a chloroform solvent
  8. concentrationfollowed by concentration
  9. customto obtain the intended product

Sources & evidence

ORD record
ord-0d421c44a88a41a2b3664dae38605673
Source dataset
uspto-grants-2010_09
Patent number
US07799894B2

Reaction notes

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