Ethoxyethylamine → N-(2-ethoxyethyl)-2-chloro-6-(trimethylsilyl)benzamide

HRID 368614

Reaction equation

HRID 368614 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Si:11]([CH3:14])([CH3:13])[CH3:12])[C:3]=1[C:4](Cl)=[O:5].[CH2:15]([O:17][CH2:18][CH2:19][NH2:20])[CH3:16]>C1(C)C=CC=CC=1>[CH2:15]([O:17][CH2:18][CH2:19][NH:20][C:4](=[O:5])[C:3]1[C:7]([Si:11]([CH3:14])([CH3:13])[CH3:12])=[CH:8][CH:9]=[CH:10][C:2]=1[Cl:1])[CH3:16]

Participants

4

Reactant 2

HCID 66970EthoxyethylamineHCID 151835572-Chloro-6-(trimethylsilyl)benzoyl chloride

Product 1

HCID 18630026N-(2-ethoxyethyl)-2-chloro-6-(trimethylsilyl)benzamideYield 66.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The compound of Example b (4.94 g, 20 mmol), 2-ethoxyethyl amine (3.92 g, 44 mmol), and toluene (35 mL) were combined according to General Method E1. The crude product was recrystallized from aq ethanol to afford 3.97 g of N-(2-ethoxyethyl)-2-chloro-6-(trimethylsilyl)benzamide as white solid, a 66% yield. m.p. 71-73° C.

Workup

  1. customThe crude product was recrystallized from aq ethanol

Sources & evidence

ORD record
ord-7c7469ef38f34e528b1eecd2407de8d7
Source dataset
uspto-grants-2000_10
Patent number
US06133252

Linked notes

Loading…