Water → 2,2'-(2,5-Dioxopiperazine-1,4-diyl)diacetic acid

HRID 1859259Notes

Reaction equation

HRID 1859259 reaction equation
[C:1]([N:4]([CH2:9][C:10]([OH:12])=O)[CH2:5][C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].[OH2:13]>C(O)(=O)C>[C:6]([CH2:5][N:4]1[CH2:2][C:1](=[O:3])[N:4]([CH2:5][C:6]([OH:8])=[O:7])[CH2:9][C:10]1=[O:12])([OH:7])=[O:13]

Participants

4

Reactant 2

HCID 962WaterHCID 10130190N-acetyliminodiacetic acid

Product 1

HCID 235108522,2'-(2,5-Dioxopiperazine-1,4-diyl)diacetic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
195 °C

Procedure

N-acetyliminodiacetic acid (XVI) monohydrate (45 g) and varying amounts of water and acetic acid were heated at 175° C. or 195° C. for various periods of time. After cooling to room temperature, the mixture was filtered. The solid was washed with water (10 mL) and dried to give 1,4-di(carboxymethyl)-2,5-diketopiperazine. The table below shows the yields of solid under various conditions.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered
  3. washThe solid was washed with water (10 mL)
  4. customdried

Sources & evidence

ORD record
ord-17dfbc30ca9d4fd8b1bb1863a4fe8c94
Source dataset
uspto-grants-2000_11
Patent number
US06153753

Reaction notes

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