Hydrochloric Acid → 1,3-Bis(carboxymethyl)-1H-imidazol-3-ium chloride

HRID 538737Notes

Reaction equation

HRID 538737 reaction equation
[Cl-:1].C[O:3][C:4](=[O:16])[CH2:5][N:6]1[CH:10]=[CH:9][N+:8]([CH2:11][C:12](=[O:15])[O:13]C)=[CH:7]1.Cl>>[Cl-:1].[C:12]([CH2:11][N:8]1[CH:9]=[CH:10][N+:6]([CH2:5][C:4]([OH:16])=[O:3])=[CH:7]1)([OH:15])=[O:13]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 867627401,3-Bis(2-methoxy-2-oxoethyl)-1H-imidazol-3-ium chloride

Product 1

HCID 867627421,3-Bis(carboxymethyl)-1H-imidazol-3-ium chlorideYield 87.7%

Procedure

To 1,3-bis(2-methoxy-2-oxoethyl)-1H-imidazol-3-ium chloride (9; 41.00 g, 164.88 mmol, 1 eq.) was added 37% aq. HCl (30.03 mL, 362.74 mmol, 2.2 eq.). The mixture was stirred under reflux for 0.5 hour. The mixture was concentrated and the remaining solid was washed with acetone (2×200 mL) and Et2O (3×200 mL). Drying in in vacuo gave 10 (31.89 g, 144.55 mmol, 87.7%) as a white solid.

Workup

  1. temperatureunder reflux for 0.5 hour
  2. concentrationThe mixture was concentrated
  3. washthe remaining solid was washed with acetone (2×200 mL) and Et2O (3×200 mL)
  4. customDrying in in vacuo

Sources & evidence

ORD record
ord-06b398af278c436b992f58267a0d1b26
Source dataset
uspto-grants-2014_10
Patent number
US08865757B1

Reaction notes

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