Hydrochloric Acid → HCID 54381897, compound

HRID 343278Notes

Reaction equation

HRID 343278 reaction equation
[NH:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].C([O:14][C:15](=[O:20])[C:16]([CH2:18][OH:19])=[CH2:17])C.Cl>O>[C:15]([CH:16]([CH2:18][OH:19])[CH2:17][N:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4])([OH:20])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8897Iminodiacetic acidHCID 14798Sodium Hydroxide2×HCID 24827Acrylic acid, 2-(hydroxymethyl)-, ethyl ester

Product 1

HCID 54381897HCID 54381897, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

(0.05 mole) of iminodiacetic acid were suspended in 25 ml of water and neutralized with sodium hydroxide to pH=10-12. 6.5 g. (0.05 mole) of ethyl--2--hydroxymethylacrylate was added dropwise to the solution and the temperature of the resulting mixture increased to 80°C. 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 to room temperature and acidified to pH=1.5 with concentrated hydrochloric acid. The solvent was distilled under reduced pressure to half the weight of the solution and the product was allowed to crystallize. The white precipitate was filtered, washed with water and methanol and then dried in a vacuum to 5.3 g. of white powder. The yield was 45% of theoretical and the product had a melting point of 195 °C.

Workup

  1. temperaturecooled to room temperature
  2. distillationThe solvent was distilled under reduced pressure to half the weight of the solution
  3. customto crystallize
  4. filtrationThe white precipitate was filtered
  5. washwashed with water and methanol
  6. customdried in a vacuum to 5.3 g

Sources & evidence

ORD record
ord-8ce7eb29e8934bcda84a64b73a843faa
Source dataset
uspto-grants-1999_01
Patent number
US05861369

Reaction notes

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