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

HRID 260417Notes

Reaction equation

HRID 260417 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 of 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 of triethylamine were dissolved in 16 mL of dry tetrahydrofuran. 1.63 g of 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.

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-e83fd7405009452894335135ffaf77bf
Source dataset
uspto-grants-1996_06
Patent number
US05527862

Reaction notes

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