Toluene → HCID 66990270, compound

HRID 2354312Notes

Reaction equation

HRID 2354312 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)[CH:2]=[CH2:3].[Cl:23][SiH:24]([Cl:26])[Cl:25].C1(C)C=CC=CC=1>C(Cl)Cl>[C:11]1([N:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7]2[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH2:3][Si:24]([Cl:26])([Cl:25])[Cl:23])=[CH:5][CH:6]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24811TrichlorosilaneHCID 16218147N,N-Diphenyl-4-(prop-2-en-1-yl)aniline

Product 1

HCID 66990270HCID 66990270, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 17 (0.18 g, 0.65 mmol) in 25 mL dry CH2Cl2 at 25° C. under inert atmosphere was added H2PtCl6.xH2O (0.001 g), followed by trichlorosilane (0.88 g, 6.5 mmol). The reaction solution was warmed to 30° C. and monitored by NMR until the completion of reaction after 4 h. Removal of the solvent in vacuum yielded a oil. 20 mL dry toluene was added to the residue and filtered into a Schlenk flask by cannula. The filtrate was concentrated under vacuum to give 18 as a oil. Yield, 98%. 1H NMR (benzene): δ0.90 (t, J=8 Hz, 2H), 1.55 (m, 2H), 2.20 (t, J=8 Hz, 2H), 6.75-6.83 (m, 4H), 6.98-7.14 (m, 10H).

Workup

  1. custommonitored by NMR until the completion of reaction after 4 h
  2. customRemoval of the solvent in vacuum
  3. customyielded a oil
  4. filtrationfiltered into a Schlenk flask by cannula
  5. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-b16d1e778c1a4d698c749e7b13e6aee6
Source dataset
uspto-grants-2010_07
Patent number
US07750175B2

Reaction notes

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