4-Aminobenzonitrile → 4-[N-(4-tert-butyldimethylsilyloxybenzyl)amino]benzonitrile
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
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
- customThe procedure of Preparation Example 7