Tetrahydrofuran → HCID 131722565, compound

HRID 1700790Notes

Reaction equation

HRID 1700790 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[C:18]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.[C:33]1([N:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[NH2:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C1COCC1>CS(O)(=O)=O.CN(C)C(=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)([CH3:10])[CH3:9])=[CH:6][CH:7]=1.[C:33]1([N:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[N:40]=[C:18]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 10738Hydrazine, 1,1-diphenyl-, hydrochloride (1:1)HCID 69294901HCID 69294901, compound

Product 1

HCID 131722565HCID 131722565, compound

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 31374DimethylacetamideSolvent

Procedure

In a 100 mL single neck round bottom flask was weighed poly(bisphenol-A-benzophenone) (5.000 g, 11.50 mmol), 1,1-diphenylhydrazine hydrochloride (2.714 g, 12.30 mmol), THF (18 g) and N,N-dimethylacetamide (18 g). The flask was fitted with a condenser. The dark slurry was stirred with a magnetic stirrer to dissolve the starting materials. To the dark solution was added methanesulfonic acid (about 6 drops), and the solution heated to reflux . After stirring for about 4 hours, the orange polymer solution was precipitated in water, and chopped in a high speed blender. The yellow fibrous polymer was isolated by filtration, washed in boiling water (about 45 min.), filtered, washed in boiling methanol (about 45 min.), filtered and dried at about 100° C. for about 16 hours. The yield was about 5.29 g. The number average molecular weight of the polymer was about 11.8K.

Workup

  1. customIn a 100 mL single neck round bottom flask was weighed poly
  2. customThe flask was fitted with a condenser
  3. dissolutionto dissolve the starting materials
  4. temperaturethe solution heated to reflux
  5. stirringAfter stirring for about 4 hours
  6. customthe orange polymer solution was precipitated in water
  7. customThe yellow fibrous polymer was isolated by filtration
  8. washwashed
  9. customwater (about 45 min.)
  10. filtrationfiltered
  11. washwashed
  12. custommethanol (about 45 min.)
  13. filtrationfiltered
  14. customdried at about 100° C. for about 16 hours

Sources & evidence

ORD record
ord-1a322bcf0a654b5d8c828b13a1803043
Source dataset
uspto-grants-2002_02
Patent number
US06350553B2

Reaction notes

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