Iminodiacetic acid → HCID 53856005, compound

HRID 343279Notes

Reaction equation

HRID 343279 reaction equation
[NH:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].[OH:12][CH:13]([C:15](=[CH2:19])[C:16]([O-:18])=[O:17])[CH3:14]>O>[C:16]([CH:15]([CH:13]([OH:12])[CH3:14])[CH2:19][N:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4])([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 8897Iminodiacetic acidHCID 14798Sodium Hydroxide2×HCID 19065314HCID 19065314, compound

Product 1

HCID 53856005HCID 53856005, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

(0.1 mole) of iminodiacetic acid were suspended in 100 ml. of water and neutralized with sodium hydroxide to pH=10-12. 14.4 g (0.1 mole) ethyl----2--(1--hydroxyethyl)propenoate was added and the pH was maintained at 10-12 by further addition of sodium hydroxide. The reaction mixture was stirred at 80°C for 20 hours and then cooled at room temperature and acidified to pH=2. The solvent was distilled under reduced pressure to one-third of the weight of the solution and sodium chloride was filtered off. The filtrate was poured in 400 ml. of methanol/acetone (50/50) and the precipitate was washed with acetone and dried in vacuum to 12.3 g of a white powder. The yield was 49% of theoretical.

Workup

  1. temperaturecooled at room temperature
  2. distillationThe solvent was distilled under reduced pressure to one-third of the weight of the solution and sodium chloride
  3. filtrationwas filtered off
  4. additionThe filtrate was poured in 400 ml
  5. washof methanol/acetone (50/50) and the precipitate was washed with acetone
  6. dry with materialdried in vacuum to 12.3 g of a white powder

Sources & evidence

ORD record
ord-8d6c7329c91340a59fcb04bd66c60488
Source dataset
uspto-grants-1999_01
Patent number
US05861369

Reaction notes

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