Dimethyl Sulfoxide → HCID 86612732, compound

HRID 1715542Notes

Reaction equation

HRID 1715542 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:3]=1[N:4]=[C:5]1[C:10](=[N:11]2)[C:9]2[CH:16]=[CH:17][CH:18]=[CH:19][C:8]=2[C:7]2[CH:20]=[CH:21][CH:22]=[CH:23][C:6]1=2.F[C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1.CS(C)=O.C(O[K])(C)(C)C>O>[N+:31]([C:28]1[CH:29]=[CH:30][C:25]([N:4]2[C:3]3[C:12](=[CH:13][CH:14]=[CH:15][C:2]=3[NH2:1])[NH:11][C:10]3[C:9]4[CH:16]=[CH:17][CH:18]=[CH:19][C:8]=4[C:7]4[CH:20]=[CH:21][CH:22]=[CH:23][C:6]=4[C:5]2=3)=[CH:26][CH:27]=1)([O-:33])=[O:32]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 9590p-FluoronitrobenzeneHCID 23146832HCID 23146832, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 86612732HCID 86612732, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

While agitating 10.0 g (34 mmol) of 10-aminodibenzo(A,C)phenazine, 4.8 g (34 mmol) of 4-fluoronitrobenzene and 500 ml of dimethylsulfoxide, 19.4 g (173 mmol) of t-butoxy potassium was gently added. After completion of the addition, the reaction container was charged with nitrogen, followed by agitation at room temperature for 24 hours. After completion of the reaction, 500 ml of water was added while cooling, after which the reaction solution was filtered to obtain a filtration residue. The thus obtained residue was washed with methanol to obtain the intended product.

Workup

  1. additionwas gently added
  2. additionAfter completion of the addition
  3. additionthe reaction container was charged with nitrogen
  4. additionwas added
  5. temperaturewhile cooling
  6. filtrationafter which the reaction solution was filtered
  7. customto obtain a filtration residue
  8. washThe thus obtained residue was washed with methanol
  9. customto obtain the intended product

Sources & evidence

ORD record
ord-368353d470d84efb965729c03f32ed82
Source dataset
uspto-grants-2010_09
Patent number
US07799894B2

Reaction notes

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