4-Aminobenzonitrile → 4-[N-(4-tert-butyldimethylsilyloxybenzyl)amino]benzonitrile

HRID 1883693Notes

Reaction equation

HRID 1883693 reaction equation
[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Cl)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1>>[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH:17][C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 133964-AminobenzonitrileHCID 113688854-(Tert-butyldimethylsilyloxy)benzyl chloride

Product 1

HCID 235083944-[N-(4-tert-butyldimethylsilyloxybenzyl)amino]benzonitrileYield 25.2%

Procedure

The procedure of Preparation Example 7 was repeated, except that 2.058 g of 4-(tert-butyldimethylsilyloxy)benzyl chloride was used in place of 4-benzyloxybenzyl chloride, and 0.946 g of 4-aminobenzonitrile was used in place of 4-aminophenol. The resulting crude product was purified by silica gel column chromatography (using a 3:1 mixture of hexane and ethyl acetate as the eluent) to obtain 0.682 g of 4-[N-(4-tert-butyldimethylsilyloxybenzyl)amino]benzonitrile.

Workup

  1. customThe procedure of Preparation Example 7
  2. customThe resulting crude product was purified by silica gel column chromatography (
  3. additiona 3:1 mixture of hexane and ethyl acetate as the eluent)

Sources & evidence

ORD record
ord-4a1b5682fada4cdfa98402cb4cfb26f9
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

Loading…