Chlorotrimethylsilane → 3,3'-Bis(trimethylsiloxy)-4,4'-bis(trimethylsilylamino)biphenyl

HRID 128843

Reaction equation

HRID 128843 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([OH:16])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].COC1C=C(C2C=CC(N)=C(OC)C=2)C=CC=1N.I.[CH3:36][Si:37]([CH3:40])([CH3:39])Cl>O1CCCC1.C(N(CC)CC)C>[CH3:36][Si:37]([CH3:40])([CH3:39])[O:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][Si:37]([CH3:40])([CH3:39])[CH3:36])=[C:11]([O:16][Si:37]([CH3:40])([CH3:39])[CH3:36])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[NH:8][Si:37]([CH3:40])([CH3:39])[CH3:36]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8411DianisidineHCID 169183,3'-DihydroxybenzidineHCID 24841Hydrogen iodide

Product 1

HCID 111563923,3'-Bis(trimethylsiloxy)-4,4'-bis(trimethylsilylamino)biphenyl

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

0.540 g 3,3'-dihydroxy-4,4'-diaminobiphenyl (synthesized from 3,3'-dimethoxy-4,4'-diaminobiphenyl using hydrogen iodide by the known method) and 1.52 g triethylamine were dissolved in 16 mL dry tetrahydrofuran. 1.63 g trimethylchlorosilane was then added dropwise followed by heating under reflux for 72 hours. Operating in an argon atmosphere, the salt was filtered off and the solvent, etc., was removed under reduced pressure to yield 3,3'-bis(trimethylsiloxy)-4,4'-bis(trimethylsilylamino)biphenyl. This monomer was prepared immediately prior to each of the polymerization reactions described below.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 72 hours
  3. filtrationOperating in an argon atmosphere, the salt was filtered off
  4. customthe solvent, etc., was removed under reduced pressure

Sources & evidence

ORD record
ord-6d2ce9546d3c4c3f914f14bf20ede102
Source dataset
uspto-grants-1995_11
Patent number
US05464922

Linked notes

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