p-Fluoronitrobenzene → HCID 23146836, compound

HRID 1715540Notes

Reaction equation

HRID 1715540 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:15]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[N:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[NH2:21])[N:7]=1.F[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1.C(O[K])(C)(C)C>CS(C)=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:15]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[N:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[NH:21][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)[N:7]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 22638471HCID 22638471, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 23146836HCID 23146836, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

While agitating 3.1 g (9.9 mmol) of 2,3-di(2-thienyl)-5-aminoquinoxaline, 1.4 g (9.9 mmol) of 4-fluoronitrobenzene and 15 g of dimethylsulfoxide, 3.3 g (29.6 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 14 hours. After completion of the reaction, 100 ml of water was added while cooling, and the resulting compound was filtered and dried, followed by purification with a silica gel column.

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. filtrationthe resulting compound was filtered
  8. customdried
  9. customfollowed by purification with a silica gel column

Sources & evidence

ORD record
ord-6fe6769db9994f358e1206c0377ce6f4
Source dataset
uspto-grants-2010_09
Patent number
US07799894B2

Reaction notes

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