N,N-diethyl-m-toluamide → N,N-Diethyl-5-methyl-2-(trimethylsilyl)benzamide

HRID 368582

Reaction equation

HRID 368582 reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=1)[CH3:2].[CH3:15][Si:16](Cl)([CH3:18])[CH3:17]>>[CH2:13]([N:3]([CH2:1][CH3:2])[C:4](=[O:12])[C:5]1[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][C:10]=1[Si:16]([CH3:18])([CH3:17])[CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 4284N,N-diethyl-m-toluamideHCID 6397Chlorotrimethylsilane

Product 1

HCID 18630275N,N-Diethyl-5-methyl-2-(trimethylsilyl)benzamideYield 46%

Procedure

These compounds were prepared from N,N-diethyl-3-methylbenzamide and 2.0 eq TMSCl according to General Method A. Purification by HPLC using 1:9 ethyl acetate/hexanes gave two products. Compound 63 was isolated as 6.0 g of a clear oil, a 46% yield. Compound 64 was isolated as 2.3 g of a clear oil, a 17% yield.

Workup

  1. customPurification by HPLC
  2. customgave two products

Sources & evidence

ORD record
ord-821f8b5598434dcaa2d02e9295f7a63a
Source dataset
uspto-grants-2000_10
Patent number
US06133252

Linked notes

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