Lactic Acid → N,N'-1,2-ethanediylbislactamide

HRID 865906

Reaction equation

HRID 865906 reaction equation
[C:1]([OH:6])(=O)[CH:2]([CH3:4])[OH:3].[CH2:7]([NH2:10])[CH2:8][NH2:9]>O>[CH2:7]([NH:10][C:1](=[O:6])[CH:2]([CH3:4])[OH:3])[CH2:8][NH:9][C:1](=[O:6])[CH:2]([CH3:4])[OH:3]

Participants

4

Conditions

Temperature
125 °C

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.

Workup

  1. customequipped with a distillation head
  2. additionDuring the course of the addition
  3. customreached 140° C
  4. customremoved by distillation
  5. additionit was poured into an aluminum pan
  6. temperatureto cool to ambient temperature
  7. customto provide 468 g of crude product
  8. customThis material was recrystallized from methanol (1.9 L)

Sources & evidence

ORD record
ord-d54f42a2529742d9bc5406ba76439fd2
Source dataset
uspto-grants-1996_10
Patent number
US05569450

Linked notes

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