Reaction #1503

Reaction equation

Lactic acid

ethylene diamine

→

N,N'-1,2-ethanediylbislactamide

Solvents

water

Conditions

Workup

1. 1
   Otherequipped with a distillation head
2. 2
   workup.ADDITIONDuring the course of the addition
3. 3
   Otherreached 140° C
4. 4
   Otherremoved by distillation
5. 5
   workup.ADDITIONit was poured into an aluminum pan
6. 6
   Temperatureto cool to ambient temperature
7. 7
   Otherto provide 468 g of crude product
8. 8
   OtherThis material was recrystallized from methanol (1.9 L)

Procedure

Lactic acid (441 g; 4.90 moles) was placed in a reaction flask equipped with a distillation head. Under a nitrogen atmosphere, ethylene diamine (147 g; 2.45 moles) was slowly added with stirring to the reaction flask. During the course of the addition, the reaction mixture turned a deep orange and the temperature reached 140° C. The reaction mixture was then heated at 150° C. overnight with the water being removed by distillation. The reaction mixture was allowed to cool to 125° C. then it was poured into an aluminum pan and allowed to cool to ambient temperature. to provide 468 g of crude product. This material was recrystallized from methanol (1.9 L) to provide N,N'-1,2-ethanediylbislactamide, m.p. 188° C.

Source