Tetrahydrofuran → HCID 86733703, compound

HRID 918228Notes

Reaction equation

HRID 918228 reaction equation
[CH:1]([N:3]1C(=O)C2=CC=CC=C2C1=O)=[CH2:2].[CH:14]([N:16]1[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH2:15].O1CCCC1.O.NN>C(O)C>[CH:1]([NH2:3])=[CH2:2].[CH:14]([N:16]1[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH2:15]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)2×HCID 86733704HCID 86733704, compound

Product 1

HCID 86733703HCID 86733703, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.6 grams of a random copolymer of N-vinylphthalimide/N-vinylcarbazole (9.2/90.8 mole percent) are dissolved in a solution containing 100 milliliters of tetrahydrofuran and 10 milliliters of ethanol. After the copolymer has been dissolved, 0.13 grams hydrazine hydrate (85%) were added and the solution thereafter heated to boiling under refluxing conditions overnight. At the end of this interval, the solution apparently remains unchanged, it retaining its characteristic yellow color. An additional 2.6 grams of hydrazine hydrate are then added and the solution refluxed for an additional two days. At the end of this time, the characteristic yellow color of the solution has disappeared and a white precipitate formed. The solution is now allowed to cool to room temperature and the precipitate removed by filtration. This precipitate is believed to be phthalhydrazide. The polymer is separated from the solution by precipitation with hexane in a Waring blender. The number average molecular weight of the polymeric product is about 78,000.

Workup

  1. dissolutionAfter the copolymer has been dissolved
  2. temperaturethe solution thereafter heated
  3. customto boiling under refluxing conditions overnight
  4. temperaturethe solution refluxed for an additional two days
  5. customa white precipitate formed
  6. customthe precipitate removed by filtration
  7. customThe polymer is separated from the solution by precipitation with hexane in a Waring blender

Sources & evidence

ORD record
ord-d3328977e96a4dbab0cbe1d504013b0f
Source dataset
uspto-grants-1976_07
Patent number
US03970602

Reaction notes

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