Benzenamine, N,N-diethyl-4-nitroso- → HCID 13680954, compound

HRID 982584Notes

Reaction equation

HRID 982584 reaction equation
[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]1[CH:9]=[CH:8][C:7]([N:10]=O)=[CH:6][CH:5]=1)[CH3:2].[C:14]1([N:20]2[C:24]([NH2:25])=[CH:23][C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)(=O)C>[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]1[CH:9]=[C:8]2[C:7]([N:10]=[C:23]3[C:22]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[N:21][N:20]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:24]3=[N:25]2)=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 67115Benzenamine, N,N-diethyl-4-nitroso-HCID 1999691,3-Diphenyl-1H-pyrazol-5-amine

Product 1

HCID 13680954HCID 13680954, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.78 g N,N-diethyl-p-nitrosoaniline and 2.65 g 1,3-diphenyl-5-aminopyrazole were refluxed for 2 hrs in acetic acid. The mixture was concentrated to half volume. Water was added to get a precipitate, then filtered. The solid was purified by chromatograph column on silica gel. After removing the solvent, 1.6 g pure 7-diethylamino-1,3-diphenyl-1H-pyrazolo[3,4-b]quinoxaline (DEDPPQ) was obtained as a brown solid.

Workup

  1. concentrationThe mixture was concentrated to half volume
  2. additionWater was added
  3. customto get a precipitate
  4. filtrationfiltered
  5. customThe solid was purified by chromatograph column on silica gel
  6. customAfter removing the solvent

Sources & evidence

ORD record
ord-ffbd9b7213634e0489f6efd0a5762555
Source dataset
uspto-grants-2005_03
Patent number
US06861162B2

Reaction notes

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