Tert-Butylamine → N-(tert-butyl)(dimethyl)(2-methyl-8H-indeno[2,1-b]thiophen-8-yl)silanamine

HRID 1868546Notes

Reaction equation

HRID 1868546 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.Cl[Si:12]([CH3:27])([CH3:26])[CH:13]1[C:21]2[S:22][C:23]([CH3:25])=[CH:24][C:20]=2[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]1=2>CCOCC.CCCCCC>[C:1]([NH:5][Si:12]([CH3:26])([CH3:27])[CH:13]1[C:21]2[S:22][C:23]([CH3:25])=[CH:24][C:20]=2[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]1=2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6385Tert-ButylamineHCID 58931541chloro(dimethyl)(2-methyl-8H-indeno[2,1-b]thiophen-8-yl)silaneHCID 178418339Butyllithium

Product 1

HCID 11985223N-(tert-butyl)(dimethyl)(2-methyl-8H-indeno[2,1-b]thiophen-8-yl)silanamine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 0.93 mL (0.0089 mol) of tert-butylamine in 30 mL of ether was treated dropwise with 5.55 mL (0.0089 mol) of 1.6M BuLi in hexane at −30° C. The reaction mixture was stirred at r.t. for 3 h and the resulting suspension was treated with a solution of 2.47 g (0.0088 mol) of chloro(dimethyl)(2-methyl-8H-indeno[2,1-b]thiophen-8-yl)silane in 10 mL of ether at −70° C. The resulting suspension was allowed to warm to r.t. and was stirred overnight. The solution was separated from LiCl and evaporated. The residue was treated with 60 mL hexane, the solution was isolated and evaporated. Yield 1.98 g (71%) of crude product as red oil.

Workup

  1. temperatureto warm to r.t.
  2. stirringwas stirred overnight
  3. customThe solution was separated from LiCl
  4. customevaporated
  5. additionThe residue was treated with 60 mL hexane
  6. customthe solution was isolated
  7. customevaporated

Sources & evidence

ORD record
ord-299023cbf0484a6a83fcca64f5cc6865
Source dataset
uspto-grants-2009_12
Patent number
US07635781B2

Reaction notes

Loading…