Triethoxysilane → 4-[N,N-bis(3,4-dimethylphenyl)amino]-[2-(triethoxysilyl)ethyl]benzene

HRID 399696Notes

Reaction equation

HRID 399696 reaction equation
[CH2:1]([O:3][SiH:4]([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])[CH3:2].[CH3:11][C:12]1[CH:13]=[C:14]([N:19]([C:28]2[CH:35]=[CH:34][C:31]([CH:32]=[CH2:33])=[CH:30][CH:29]=2)[C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([CH3:27])[CH:21]=2)[CH:15]=[CH:16][C:17]=1[CH3:18]>C1(C)C=CC=CC=1>[CH3:27][C:22]1[CH:21]=[C:20]([N:19]([C:28]2[CH:29]=[CH:30][C:31]([CH2:32][CH2:33][Si:4]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])[O:3][CH2:1][CH3:2])=[CH:34][CH:35]=2)[C:14]2[CH:15]=[CH:16][C:17]([CH3:18])=[C:12]([CH3:11])[CH:13]=2)[CH:25]=[CH:24][C:23]=1[CH3:26]

Participants

4

Reactant 2

HCID 13830TriethoxysilaneHCID 108927834-[N,N-bis(3,4-dimethylphenyl)amino]styrene

Product 1

HCID 223283174-[N,N-bis(3,4-dimethylphenyl)amino]-[2-(triethoxysilyl)ethyl]benzeneYield 94.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

40 mL of toluene, 6.0 g (37 mmol) of triethoxysilane, and 0.34 mmol of dichloro-(n-cycloocta-1,5-diene) platinum were loaded into a three-neck flask. While being stirred at room temperature, 20 mL of a toluene solution of 9.9 g of 4-[N,N-bis-(3,4-dimethylphenyl) amino] styrene was dropped into the flask. Upon completion of the addition of the drops, the mixture was stirred for 3 hours at 70° C. The solvent was removed under reduced pressure, and a lemon-yellow oily substance of 4-[N,N-bis-(3,4-dimethylphenyl) amino]-[2-(triethoxysilyl) ethyl] benzene was obtained. The amount obtained was 14.0 g (yield was 94.2%).

Workup

  1. additionUpon completion of the addition of the drops
  2. stirringthe mixture was stirred for 3 hours at 70° C
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6cd5535a7a19425ca5ae810d81231372
Source dataset
uspto-grants-1998_10
Patent number
US05824443

Reaction notes

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