Dinitrofluorobenzene → HCID 86733705, compound

HRID 918229Notes

Reaction equation

HRID 918229 reaction equation
[CH:1]([NH2:3])=[CH2:2].[CH:4]([N:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)=[CH2:5].C(=O)([O-])[O-].[K+].[K+].[N+:25]([C:28]1[CH:33]=[C:32]([N+:34]([O-:36])=[O:35])[CH:31]=[CH:30][C:29]=1F)([O-:27])=[O:26]>CN(C)C=O>[CH:1]([NH:3][C:29]1[CH:30]=[CH:31][C:32]([N+:34]([O-:36])=[O:35])=[CH:33][C:28]=1[N+:25]([O-:27])=[O:26])=[CH2:2].[CH:4]([N:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)=[CH2:5]

Participants

5

Reactant 3

HCID 6264Dinitrofluorobenzene2×HCID 11430Potassium CarbonateHCID 86733703HCID 86733703, compound

Product 1

HCID 86733705HCID 86733705, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 gram of a copolymer comprising vinylamine/N-vinylcarbazole (25/75 mole percent) is dissolved in 50 milliliters of anhydrous dimethylformamide (DMF). 0.184 grams potassium carbonate is then suspended in this polymer solution and thereafter 1 milliliter of 2,4-dinitrofluorobenzene (Sanger's reagent) added by dropwise addition. Immediately after the addition of Sanger's reagent a yellow color develops within the solution and becomes more intense as the reaction proceeds. The flask containing the solution is then heated over a steam bath for about 11/2 hours at which time the polymer precipitated from the DMF by the addition of water. The precipitate is separated from the solution by filtration and purified by washing with warm dilute aqueous potassium hydroxide solution. This washing procedure is repeated several times until the filtrate is colorless. The polymer is then dried in a vacuum oven at about 70°C. The number average molecular weight of the product is in the range of about 100,000.

Workup

  1. custombecomes more intense as the reaction proceeds
  2. additionThe flask containing the solution
  3. temperatureis then heated over a steam bath for about 11/2 hours at which time the polymer
  4. customprecipitated from the DMF by the addition of water
  5. customThe precipitate is separated from the solution by filtration
  6. custompurified
  7. washby washing
  8. temperaturewith warm dilute aqueous potassium hydroxide solution
  9. customThe polymer is then dried in a vacuum oven at about 70°C

Sources & evidence

ORD record
ord-ca1608032e5443858bf5a93970064c8a
Source dataset
uspto-grants-1976_07
Patent number
US03970602

Reaction notes

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