Reaction #215243

Reaction equation

chloroethyl methyl ether

2'-methyl-6'-ethyl-2-chloroacetanilide

THF

→

N-(1-methoxy-1-ethyl)-2'-methyl-6'-ethyl-2-chloroacetanilide

Yield 86.0%

Solvents

ether

diethyl ether

Conditions

Workup

1. 1
   OtherReaction
2. 2
   workup.ADDITIONwas added
3. 3
   Otherdidn't react although some KH

Procedure

The same general procedure of Example 32 was followed, except here the sec-amide, 2'-methyl-6'-ethyl-2-chloroacetanilide, 21.1 g (0.1 mol), was solubilized with a small amount of THF in 400-500 ml diethyl ether. Reaction went well, but gas evolved when chloroethyl methyl ether was added. However, at final addition (about 2.5×theory) the added ether didn't react although some KH was still present. Upon workup, the product, N-(1-methoxy-1-ethyl)-2'-methyl-6'-ethyl-2-chloroacetanilide, was obtained in 86% yield, b.p. 130° at 0.05 mm Hg.

Source