Reaction #4634

Reaction equation

N-(2-hydroxyethyl)-N'-(2-hydroxybenzyl)urea

potassium carbonate

epichlorohydrin

→

N-[2-(2,3-epoxypropoxy)benzyl]-N'-(2-hydroxyethyl)urea

Conditions

Workup

1. 1
   FiltrationThe solids are then suction-filtered whilst hot,
2. 2
   Washwashed with acetonitrile
3. 3
   Concentrationthe filtrate is concentrated by evaporation in vacuo
4. 4
   OtherThe oil remaining crystallises when
5. 5
   workup.WAITleft
6. 6
   Otheris recrystallised from 320 ml of ethyl acetate, with carbon treatment

Procedure

A mixture of 29.2 g of N-(2-hydroxyethyl)-N'-(2-hydroxybenzyl)urea, 440 ml of epichlorohydrin and 38.9 g of potassium carbonate is stirred for 6 hours at 90°. The solids are then suction-filtered whilst hot, washed with acetonitrile and the filtrate is concentrated by evaporation in vacuo. The oil remaining crystallises when left to stand and is recrystallised from 320 ml of ethyl acetate, with carbon treatment. The resulting epoxide melts at 96°-99°.

Source